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[ CAS No. 10147-36-1 ] {[proInfo.proName]}

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Chemical Structure| 10147-36-1
Chemical Structure| 10147-36-1
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Quality Control of [ 10147-36-1 ]

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Product Details of [ 10147-36-1 ]

CAS No. :10147-36-1 MDL No. :MFCD00007462
Formula : C3H7ClO2S Boiling Point : No data available
Linear Structure Formula :CH3CH2CH2SO2Cl InChI Key :KPBSJEBFALFJTO-UHFFFAOYSA-N
M.W : 142.60 Pubchem ID :66279
Synonyms :

Calculated chemistry of [ 10147-36-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 30.29
TPSA : 42.52 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 0.38
Log Po/w (SILICOS-IT) : 0.59
Consensus Log Po/w : 1.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.4
Solubility : 5.7 mg/ml ; 0.0399 mol/l
Class : Very soluble
Log S (Ali) : -1.77
Solubility : 2.41 mg/ml ; 0.0169 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.59
Solubility : 3.64 mg/ml ; 0.0255 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 10147-36-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 10147-36-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 10147-36-1 ]

[ 10147-36-1 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 10147-36-1 ]
  • [ 6995-79-5 ]
  • [ 108846-57-7 ]
  • 2
  • [ 10147-36-1 ]
  • [ 84832-02-0 ]
  • [ 1186193-95-2 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; General procedure: A solution of aniline (1.0 eq.) and Et3N (2.2 eq.) in dry DCM (0.25 m) was cooled to 0C and the corresponding sulfonyl chloride was added dropwise. After complete addition the ice bath was removed and the solution was stirred at room temperature for ~1 h. The solution was then diluted with water, extracted with EtOAc and the combined organic layers were dried over Na2S04. The solvent was removed under reduced pressure and the product was purified via flash chromatography (Si02, nHex/EtOAc 9/1 ).
75% With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; To a solution of compound 3 (11.5 g, 61.4 mmol) and triethylamine (25.67 mL, 184.2 mmol) in CH2Cl2 (55 mL) was added propane-1-sulfonyl chloride (17.25 mL, 153.3 mmol) dropwise at 0 C. The reaction mixture was stirred at room temperature for 1 h. Water (150 mL) was added, and the organic layer was separated, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (6:1-4:1 hexanes/EtOAc) to give 4 (18.4 g, 75%) as an off-white solid, mp 76-77 C. 1H NMR (CDCl3): δ 7.51-7.47 (m, 1H), 7.07-7.03 (m, 1H), 3.97 (s, 3H), 3.67-3.61 (m, 2H), 3.52-3.46 (m, 2H), 1.99-1.91 (m, 4H), 1.10 (t, J = 7.5 Hz, 6H).
With triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with water bath; Step C: Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J =7.4 Hz, 6H). m/z (APCI-neg) M-(SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃; for 1h; Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5 M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added, and the organic layer was separated, washed with water (2 x 300 mL), brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(7V-(propylsulfonyl)propyl- Dulfonamide)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J= 7.4 Hz, 6H). m/z (APCI-neg) M-(SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃; for 1h; Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5 M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added, and the organic layer was separated, washed with water (2 x 300 mL), brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(iV-(propylsulfonyl)propyl- sulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02- 1.89 (m, 4H), 1.10 (t, J= 7.4 Hz, 6H). m/z (APCI-neg) M-(SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃; for 1h;Cool water bath; Step C: Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(7V-(propylsulfonyl)propylsulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J = 7.4 Hz, 6H). m/z (APCI-neg) M-(SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with water bath; [00177] Step C: Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J = 7.4 Hz, 6H). m/z (APCI-neg) M-(SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃;Inert atmosphere; Cooling; Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2C12 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2S04), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(N- (propylsulfonyl)propylsulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDC13) δ 7.52-7.45 (m, 1H), 7.08-7.02 (m, 1H), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J = 7.4 Hz, 6H). m/z (APCI-neg) M- (S02Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃; for 3.5h;Cooling with ice; Methyl 2,6-difluoro-3-aminobenzoate compound 2310 (3.7 g, 0.020 mol) was dissolved in dichloromethaneTriethylamine (8.4 mL, 3.0 equiv) was added (40 mL), and propanesulfonyl chloride (4.7 mL, 2.1 mL) was added slowly under ice-cooling.Amount), stirring at room temperature for 3.5 hours, TLC test showed complete reaction. The reaction solution was quenched with water and extracted with dichloromethane for 3 times.Phase, 1M hydrochloric acid, saturated aqueous sodium bicarbonate solution, washed with water, saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressureThe oily compound 2311a was used in the next step without further purification.
With triethylamine; In dichloromethane; at 20℃;Cooling with water bath; Propane- 1-sulfonyl chloride (23.46 niL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate/hexanes. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(N-(propylsulfonyl) propylsulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J = 7.4 Hz, 6H). m/z (APCI-neg) M-(SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃;Cooling; Step C: propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate/hexanes. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(N- (propylsulfonyl)propylsulfonamido)-benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J = 7.4 Hz, 6H). m/z (APCI-neg) M- (SO2Pr) = 292.2.
With triethylamine; In dichloromethane; at 20℃;Cooling with water bath; Propane- 1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL, 0.5M) maintained in a cool water bath. The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2 X 300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% ethyl acetate ("EtOAc")/hexane. The isolated fractions were triturated with hexanes to afford methyl 2,6-difluoro-3-(N- (propylsulfonyl)propylsulfonamido)benzoate as a solid (24.4 g, 73% yield for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, IH), 7.08-7.02 (m, IH), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J = 7.4 Hz, 6H). m/z (APCI-neg) M- (SO2Pr) = 292.2.
24.4 g With triethylamine; In dichloromethane; at 20℃; for 1h; Propane-1-sulfonyl chloride (23.46 mL, 209.3 mmol) was slowly added to a cooled solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (15.66 g, 83.7 mmol) and triethylamine (35.00 mL, 251.1 mmol) in CH2Cl2 (175 mL). The reaction mixture was stirred for 1 hour at room temperature. Water (300 mL) was added and the organic layer was separated, washed with water (2*300 mL) and brine (200 mL), then dried (Na2SO4), filtered and concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% EtOAc/hexanes to afford methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate as a solid (24.4 g, 73% for 3 steps). 1H NMR (400 MHz, CDCl3) δ 7.52-7.45 (m, 1H), 7.08-7.02 (m, 1H), 3.97 (s, 3H), 3.68-3.59 (m, 2H), 3.53-3.45 (m, 2H), 2.02-1.89 (m, 4H), 1.10 (t, J=7.4 Hz, 6H).

  • 3
  • [ 10147-36-1 ]
  • [ 1262198-07-1 ]
  • [ 1269233-07-9 ]
YieldReaction ConditionsOperation in experiment
In pyridine; Step 4. Preparation of N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide To a solution of <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> (425 mg, 2.04 mmol) in dry pyridine (2.0 mL) was added 1-propanesulfonyl chloride (275 μL, 2.45 mmol) and the resulting reaction was maintained overnight at room temperature. The reaction was partitioned between EtOAc and water, and the layers separated. The aqueous portion was extracted with EtOAc and the combined organic portions were washed with 10% aqueous citric acid solution, water, brine, dried (Na2SO4), and concentrated to yield a brown viscous oil as a 2:1 mixture of <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> and N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide which was carried forward without further purification: N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide LCMS(m/z) not ionized (MH+); tR=1.06 minutes.
  • 4
  • [ 10147-36-1 ]
  • [ 1268830-91-6 ]
  • [ 1268830-93-8 ]
YieldReaction ConditionsOperation in experiment
85% With pyridine; dmap; In dichloromethane; at 20.0℃; for 14.0833h; Step C: A 250 mL round bottom flask was charged with a solution of methyl 3-amino-6- fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). To this reaction mixture was added a solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) over a course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, 100 mL saturated aqueous sodium bicarbonate was added followed by stirring for 10 minutes. The aqueous mixture was extracted with 200 mL ethyl acetate (2x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0-30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)benzoate as an oil (4.914 g, 85%). 1U NMR (400 MHz, DMSO-J6) delta = 9.27 (s, IH), 7.48 (dd, J=9.1, 6.1, IH), 7.09 (t, J=9.0, IH), 3.89 (s, 3H), 3.85 - 3.74 (m, 3H), 3.29 (s, 15H).
85% With pyridine;dmap; In dichloromethane; at 20.0℃; for 14.0833h; A 250 mL round bottom flask was charged with a solution of methyl 3- amino-6-fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). To this reaction mixture was added a solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) over a course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, 100 mL saturated aqueous sodium bicarbonate was added followed by stirring for 10 minutes. The aqueous mixture was extracted with 200 mL ethyl acetate (2x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0-30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, DMSOd6) delta = 9.27 (s, IH), 7.48 (dd, J=9.1, 6.1, IH), 7.09 (t, J=9.0, IH), 3.89 (s, 3H), 3.85 - 3.74 (m, 3H), 3.29 (s, 15H).
85% With pyridine; dmap; In dichloromethane; at 20.0℃; for 14.0h; A 250 mL round bottom flask was charged with a solution of <strong>[1268830-91-6]methyl 3-amino-6-fluoro-2-methoxybenzoate</strong> (3.656 g, 18.36 mmol) in methylene chloride (100 mL). A solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) was added to the reaction mixture over the course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, saturated aqueous sodium bicarbonate (100 mL) was added followed by stirring for 10 minutes. The aqueous mixture was extracted twice with ethyl acetate (200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0- 30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)- benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, (CD3)2SO) delta = 9.27 (s, 1H), 7.48 (dd, J=9.1, 6.1, 1H), 7.09 (t, J=9.0, 1H), 3.89 (s, 3H), 3.85 - 3.74 (m, 3H), 3.29 (s, 15H).
  • 5
  • [ 10147-36-1 ]
  • [ 120100-15-4 ]
  • [ 1307272-35-0 ]
YieldReaction ConditionsOperation in experiment
89% With pyridine; at 0 - 30℃; for 6.5h;Inert atmosphere; To a solution of <strong>[120100-15-4]methyl 3-amino-2-chlorobenzoate</strong> (40 g, 216 mmol) in pyridine (45 mL) stirred at 0C was added a solution of propane-1 -sulfonyl chloride (29.1 mL, 259 mmol) dropwise during 30 min. The reaction mixture was stirred at 30 C for 6 h. After 6 h, the reaction mixture was cooled and 80 mL of water and dichloromethane (100 mL) was added. The organic layer was separated and aqueous layer was extracted with dichloromethane(100 mL x 3). The combined organic layers were dried over Na2SO4, and concentrated. The residue was purified silica gel chromatography and was eluted with Hex/EtOAc (4:1 ) to afford methyl 2-chloro-3- (propylsulfonamido)benzoate. (56g, 89 % yield) as a yellow solid MS: 309 [M+H]+
  • 6
  • [ 10147-36-1 ]
  • [ 1437316-91-0 ]
  • [ 1392429-92-3 ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; In 1,2-dichloro-ethane; for 2.0h;Reflux; N-(2,4-difluoro-3-iodophenyl)propane-l -sulfonamideTo a solution of <strong>[1437316-91-0]2,4-difluoro-3-iodoaniline</strong> (255mg, lmmol) in 1,2-dichloroethane (3 mL) was added pyridine (lmL), followed by propane- 1-sulfonyl (157mg, 1. lmmol) and the resulting reaction mixture was heated to refluxing for 2 hrs. The solvent was removed in vacuo. The residue was dissolved in EtOAc, washed with aqueous NaHC03, brine, dried over Na2S04, filtered and concentrated in vacuo to afford the desired product (298mg, 83%>).1H NMR (CDCI3): ? 7.56-7.58 (1H, m), 6.90-6.95 (1H, m), 6.44 (1H, br), 3.03-3.07 (2H, m),1.84-1.90 (2H, m), 1.03-1.07 (3H, m).
83% With pyridine; In 1,2-dichloro-ethane; for 2.0h;Reflux; To a solution of <strong>[1437316-91-0]2,4-difluoro-3-iodoaniline</strong> (255 mg, 1 mmol) in 1,2_dichloroethane (3 mL) was slowly added dropwise a solution of P to pyridine (lmL), propylsulfonyl chloride (157 mg, 1. lmmol). The reaction solution was heated under reflux for 2 hours, cooled and concentrated in vacuo to remove the solvent. The resulting oil was dissolved in ethyl acetate (20 mL) and washed with 5% sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give N- (2,4-difluoro-3- Iodophenyl) propane-1-sulfonamide (298 mg, 83%).
  • 7
  • [ 10147-36-1 ]
  • [ 84832-02-0 ]
  • [ 1186223-50-6 ]
YieldReaction ConditionsOperation in experiment
54% With pyridine; In 1,2-dichloro-ethane; at 100℃; for 5h; Step 5: methyl 2,6-difluoro-3-(propylsulfonamido)benzoateTo a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (26.3 g, 0.14 mol) in 1 ,2-dichloroethane (50 mL) was added pyridine (50 mL), followed by propane- 1-sulfonyl chloride (22.0 g, 0.154 mol) and the resulting reaction mixture was heated to 100C for 5 hrs. The mixture was diluted with water, extracted with CH2CI2, washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified with column chromatography (Petrol ether: EtOAc = 3 : 1 to 1 : 1) to afford the desired product (22.3 g, 54%).1H NMR (CDCI3): ? 7.74-7.69 (1H, m), 7.02-6.97 (1H, m), 6.45 (1H, br), 3.98 (3H, br), 3.08-3.04 (2H, m), 1.93-1.83 (2H, m), 1.06 (3H, t, J = 7.6 Hz).
54% With pyridine; In 1,2-dichloro-ethane; at 100℃; for 5h; To a solution of 2,6-difluoro-3-aminobenzoate (26.3 g, 0.14 mol) in pyridine / dichloroethane (1: 1) was added dropwise a solution of sulfonyl chloride (22.0 g, 0.154 mol) , And the resulting reaction solution was stirred at 100 C for 5 hours. The solvent was removed in vacuo and the resulting residue was isolated by column chromatography (petroleum ether / ethyl acetate) to give the title compound (22.3 g, 54%).
  • 8
  • [ 10147-36-1 ]
  • [ 98-02-2 ]
  • [ 4437-20-1 ]
  • C8H12O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48%Chromat.; 9%Chromat. With triethylamine; In diethyl ether; at 20℃; for 0.333333h;Sonication; General procedure: Triethylamine (5.2 mmol) was added to a 10 mL two-neck flask containing 2-methyl-2-propanethiol (5 mmol) dissolved in anhydrous diethyl ether (2 mL). Then propane-1-sulfonyl chloride (5 mmol) was added drop-wise at room temperature. The flask wasfitted with a condenser jointed an anhydrous calcium chloride tube and was placed in anultrasound bath, where the mixture of reactants was exposed to ultrasound irradiation for aspecified period of time (20 min). After the reaction was completed, themixture was pouredinto a separatory funnel and washed with de-ionized water until a neutral pH. The organiclayer was dried over Na2SO4. After removal of the solvent by rotational evaporation, the remaining crude product was analyzed by GC/MS. The desired product was purified bysilica gel column chromatography and eluted by hexane and dichloromethane, and thenwas analyzed by NMR spectroscopy.
  • 9
  • [ 10147-36-1 ]
  • [ 6358-77-6 ]
  • N-(5-bromo-2-methoxyphenyl)propane-1-sulfonamide [ No CAS ]
  • 10
  • [ 10147-36-1 ]
  • [ 105655-01-4 ]
  • 6-bromo-4-(propylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With pyridine; at 50℃; for 2.5h;Inert atmosphere; To a solution of 3e (44.0 mg, 0.22 mmol) in pyridine (1 mL) was added 1- propanesulfonyl chloride (0.04 mL, 0.33 mmol) under argon, and the mixture was stirred at 50C for 2.5 h. After being quenched with 1 N HC1(aq) (1.0 mL) and water, EtOAc were added, and the layers were separated. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 10:90 to 20:80) to give 6e (49.6 mg, 70%) as a brown solid; ?H NMR (CDC13, 500 MHz) 7.76 (1 H, d, J = 2.3 Hz), 7.13 (1 H, dd, J = 8.6, 2.3 Hz), 6.79 (1 H, d, J = 8.6 Hz), 4.26 (2 H, t, J = 4.6 Hz), 3.85 (2 H, t, J = 4.6 Hz), 3.09-3.06 (2 H, m), 1.92-1.85 (2 H, m), 1.06(3 H, t, J= 7.4 Hz); ?3C NMR (CDC13, 125 MHz) 145.0, 128.1, 125.6, 124.3, 119.2, 113.0, 64.7, 54.0, 44.0, 17.0, 12.9.
  • 11
  • [ 10147-36-1 ]
  • [ 436-77-1 ]
  • 7O-1”-propanesulfonylfangchinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% General procedure: To a solution of compound 1 (608 mg, 1 mmol) in DCM (8 mL), TEA (152 mg, 1.5 mmol) wasadded. The mixture was stirred for 30 min at ambient temperature, then the appropriate acyl orsulfonyl chloride (1.1 mmol) was added. The mixture was stirred for 1-5 h at ambient temperatureuntil TLC indicated the completion of the reaction. The reaction mixture was diluted with water andextracted with DCM (2 Chi 30 mL). The combined organic phase was washed with water and brine, dried over anhydrous Na2SO4 and filtered, followed by solvent removal. The residue was purifiedover by flash chromatography over silica gel using a DCM/MeOH gradient as the eluent, to givecompounds 4c-4e, 5a or 5b.
  • 12
  • [ 10147-36-1 ]
  • [ 84832-02-0 ]
  • [ 1103234-56-5 ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; In dichloromethane; at 0 - 20℃; The aniline 76 (1.7 g, 8.8 mmol, 1.0 eq.) was dissolved in DCM(0.25 M), treated with TEA (2.0 g, 19.4 mmol, 2.2 eq.) and cooled to0 C. Propane-1-sulfonyl chloride (2.8 g, 19.4 mmol, 2.2 eq.) wasadded slowly to the solution at 0 C. The ice bath was removed, andthe reaction was stirred at RT until TLC revealed completion of thereaction. Water was added, and the mixture was extracted withEtOAc. The combined organic phases were dried over Na2SO4. Thesolvent was evaporated under reduced pressure, and the intermediaryformed disulfonamide was purified using flash chromatography(SiO2, nHex/EtOAc 9/1, v/v). This intermediatewas suspendedin THF/MeOH (4/1, v/v, 1 M), and aqueous 2 M NaOH solution(13 ml, 26 mmol, 3.0 eq.)was added and stirred at RT overnight. Theorganic solvents were evaporated, and the residue was acidifiedwith aqueous 1 M HCl solution. The thus formed precipitate wasfiltered off, washed with water, and the white solid was dried invacuum to dryness. Yield: 1.7 g, 6.0 mmol, 68% (over two steps). 1HNMR (DMSO-d6, 200 MHz, ppm): d 14.01 (s, 1H), 9.74 (s, 1H), 7.54(dd, J 14.8, 8.7 Hz, 1H), 7.20 (t, J 9.2 Hz, 1H), 3.15e3.02 (m, 2H),1.85e1.63 (m, 2H), 0.97 (t, J 7.4 Hz, 3H); 13C NMR (DMSO-d6,50 Hz, ppm): d 161.8,157.3 (dd, J 174.8, 6.9 Hz),152.3 (dd, J 178.1,6.9 Hz), 129.8 (dd, J 10.2, 2.2 Hz), 122.0 (dd, J 13.5, 3.8 Hz), 112.8 (dd, J 21.3, 19.3 Hz), 112.3 (dd, J 22.6, 4.1 Hz), 53.8, 16.9, 12.6.[M H]-: 278,0.
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