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[ CAS No. 1457-92-7 ] {[proInfo.proName]}

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Chemical Structure| 1457-92-7
Chemical Structure| 1457-92-7
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Product Details of [ 1457-92-7 ]

CAS No. :1457-92-7 MDL No. :MFCD00126471
Formula : C7H6N2S Boiling Point : -
Linear Structure Formula :- InChI Key :IYZKISWGGPKREZ-UHFFFAOYSA-N
M.W : 150.20 Pubchem ID :2781262
Synonyms :

Calculated chemistry of [ 1457-92-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.38
TPSA : 54.02 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.239 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.93
Solubility : 0.178 mg/ml ; 0.00118 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.97
Solubility : 0.162 mg/ml ; 0.00108 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 1457-92-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1457-92-7 ]

* 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 [ 1457-92-7 ]

[ 1457-92-7 ] Synthesis Path-Downstream   1~10

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YieldReaction ConditionsOperation in experiment
96% With N-Bromosuccinimide; In tetrachloromethane; 4-Bromomethyl-2,1,3-benzothiadiazole A mixture of <strong>[1457-92-7]4-methyl-2,1,3-benzothiadiazole</strong> (6.0 g, 40 mmol) and N-bromosuccinimide (7.12 g, 40 mmol) in carbon tetrachloride (80 mL) was refluxed under irradiation with a sunlamp for 8 hours. After cooling with ice-water bath, the succinimide was filtered off and the filtrate was washed with saturated Na2S2O3, brine, dried over Na2SO4. After removal of solvent pure 4-bromomethyl-2,1,3-benzothiadiazole (8.8 g, 96%) was obtained as a light-yellow crystalline powder. Rf=0.45 (hexane/ethyl acetate=4:1); 1H NMR (200 MHz, CDCl3) δ5.00 (s, 2H), 7.57 (m, 2H), 7.98 (d, J1=8.5 Hz, J2=1.2 Hz, 1H); HRMS: Calcd. for C7H5BrN2S 227.9357, found 227.9395.
69% With N-Bromosuccinimide; hydrogen bromide; In 1,1,2,2-tetrachloroethylene; for 6h;Reflux; 15.3 g (102 mmol) of 13 and N-bromosuccinimide (18.86 g/106 mmol/ 1.05 equ.) were dissolved in 200 mL oftetrachlorethylen and 3 droplets of hydrobromic acid (62%) were added. Theresulting brown solution was stirred under reflux over 6 h, as indicatedby TLC (AlOx; toluene:n-heptane /1:1). After cooling to room temperature, an aqueous solution of Na2S2O3was added. The organic phase was extracted with Na2CO3-solutionand water, dried over MgSO4 and concentrated under reduced pressure.The resulting thick solution was diluted with n-pentane and the product crystallized as colorless needles(16.2 g, 71 mmol, 69%). m. p.: 70-72C. 1H-NMR (250 MHz, CDCl3):δ = 7.98 (d, J = 8.7 Hz, 1H), 7.65 (d, J = 6.8 Hz, 1H), 7.61 -7.50 (m, 1H), 5.00 (s, 2H) ppm. 13C-NMR (63 MHz, CDCl3):δ = 155.25, 153.53, 131.00, 129.46, 129.44, 122.09, 77.16, 28.49 ppm. MS (EI): m/z = 228 [M+], 230 [(M+2)+],149 [(M-Br)+]. EA calc. for C7H5BrN2S:C, 36.70; H, 2.20; N, 12.23; found: C, 36.89; H, 2.11; N, 12.35.
41% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In dichloromethane; at 50℃; for 12h;Reflux; Take compound XD-2 (1.54g) and dissolve it in dichloromethane (50mL),Add N-bromosuccinimide (NBS, 2.2g)And azobisisobutyronitrile (AIBN, 85mg),The reaction was heated to reflux, and the reaction was stopped after 12 hours.The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 100:1),A white solid compound XD-3 (977 mg) was obtained.
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YieldReaction ConditionsOperation in experiment
92% With hydrogen bromide; bromine; at 80 - 130℃;Inert atmosphere; The above compound (1-f) 9.3 g was added to a 500 mL two-necked flask equipped with a reflux tube and a dropping funnel.(62 mmol) and HBr (65 mL) were stirred under an argon atmosphere. Slowly add 10 g of bromine to the obtained reaction solution.(62.6 mmol), stirred at 80 C for 30 minutes,Then, stir at 130 C.Next, the reaction solution was naturally cooled to room temperature.Then, a saturated aqueous solution of Na 2 SO 3 was added to the reaction solution for neutralization.The neutralized reaction solution is extracted with dichloromethane.The organic layer is dried with sodium sulfate and then concentrated and dried to cure.The above compound (1-g) was obtained as a yellow solid (yield: 13.2 g, yield: 92%).
86% With hydrogen bromide; bromine; In water; at 120℃; for 24h; Intermediate 1 (32.06g, 213.43mmol, 1.0 equivalent), hydrogen bromide solution (200mL, 48% aqueous solution) and bromine water (11.48mL, 224.10mmol, 1.05 equivalent) were added in sequence with magnetic force In a stirred, dry three-necked flask, put the mixture in an oil bath and stir the reaction at 120C.After 24 hours, the reaction was monitored by thin layer chromatography until the reaction was complete.The resulting mixture was cooled to room temperature and neutralized with saturated sodium bicarbonate solution.The mixture was extracted three times with ethyl acetate.The combined organic phase was washed with water, dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 20:1-5:1) to obtain 42.05 g of a white solid with a yield of 86%.
62% With bromine; In water; acetic acid; at 50 - 70℃; for 5h; 13 (2.7 g, 18 mmol) was diluted with17.5 mL of a mixture of acetic acid and water (6:1) and bromine(1 mL, 19.5 mmol, 1.1 eq.) diluted with 2 mL ofacetic acid was added drop wise at 50C under stirring. After stirring at60-70C for 5 h, water was added to the slurry. The precipitate wasfiltrated, washed with Na2S2O3-solution andwater. Recrystallization from ethanol afforded 11 as white needles (2.6 g, 11 mmol, 62%). m.p.:135-136C. 1H-NMR (250 MHz, CDCl3): δ = 7.71 (d, J= 7.3 Hz, 1H), 7.23 (d, J = 7.3 Hz, 1H), 2.69 (s, 3H) ppm. 13C-NMR(63 MHz, CDCl3): δ = 155.27, 153.30, 132.17, 131.39, 128.74, 111.30,77.16, 17.81 ppm. MS (EI): m/z = 228 [M+], 230 [(M+2)+],149 [(M-Br)+]. EA calc. for C7H5BrN2S:C, 36.70; H, 2.20; N, 12.23; found: C, 36.61; H, 2.21; N, 12.42.
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YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; thionyl chloride; In pyridine; 4-Methyl-2,1,3-benzothiadiazole Thionyl chloride (166 g, 1.4 mol) was added to a solution of 2,3-diaminotoluene (71 g, 0.58 mol) in pyridine (430 mL) dropwise at a temperature below 45 C. Concentrated HCl (300 mL) was then added dropwise while care was taken to ensure that the reaction temperature did not exceed 65 C. After cooling to room temperature, the reaction mixture was subjected to a steam distillation. The light-yellow oil suspension in the water layer was extracted with diethyl ether. The combined extracts were washed with brine and dried over Na2SO4. After removal of the solvent by rotary evaporation, 4-methyl-2,1,3-benzothiadiazole was obtained as a light-yellow liquid in 92% (80.6 g) of yield. Rf=0.62 (hexane/ethyl acetate=3:1); 1H NMR (200 MHz, CDCl3) δ2.74 (s, 3H), 7.34 (m, 1H), 7.48 (d,J1=8.7 Hz, J2=6.7 Hz, 1H), 7.83 (m, 1H).
89% Combine 3-methyl-1,2-phenylenediamine (30.53g, 249.87mmol, 1.0 equivalent), triethylamine (138.92mL, 999.47mmol, 4.0 equivalent) and dichloromethane (300mL) Add a dry three-necked flask equipped with magnetic stirring and place in an ice bath.The mixture was stirred for more than 1 hour, and then thionyl chloride (36.25 mL, 499.74 mmol, 2.0 equivalents) and dichloromethane (100 mL) were slowly added dropwise. The mixture was stirred at this temperature for 1 hour and then the mixture was placed in an oil bath. After stirring for 20 hours at 40C, the reaction was monitored by thin layer chromatography until the reaction was completed.The reaction was stopped and the resulting mixture was cooled to room temperature and quenched by adding water.The mixture was extracted three times with ethyl acetate.The combined organic phase was washed with water, dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1-4:1) to obtain 33.40 g of a colorless liquid with a yield of 89%.
77% With thionyl chloride; triethylamine; In dichloromethane; at 45℃; for 7h;Cooling with ice; Take compound XD-1 (2.26g) and dissolve it in DCM (60mL),Add triethylamine (Et3N, 10.3mL),Stir at room temperature until the solid is completely dissolved,Slowly drip thionyl chloride (SOCl2, 2.7mL) under ice bath,Heat in an oil bath at 45C for 7 hours and stop heating.The solvent was evaporated under reduced pressure, water (70mL) was added,Adjust the pH to 1 with 1N hydrochloric acid, and extract with ethyl acetate (30mL x 3),Dry with anhydrous sodium sulfate.The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1).Compound XD-2 (2.1 g) was obtained as a yellow oil.
63% With pyridine; thionyl chloride; at 30℃;Cooling with ice; Inert atmosphere; To the 500 mL two-necked flask to which the dropping funnel was attached, 12 g (98 mmol) of the above compound (1-e) and 100 mL of pyridine were added, and the mixture was stirred under ice cooling under an argon atmosphere.Thionyl chloride 16.4 mL (240 mmol) was slowly added dropwise so that the liquid temperature did not exceed 30 C. Next, 48 mL of concentrated HCl was slowly added dropwise so that the liquid temperature did not exceed 60 C, and the mixture was stirred at room temperature. Water was added to the reaction liquid, and the mixture was extracted with ether to give the compound (1-f) (yield: 9.3 g, yield: 63%) as a brown oily liquid.
44% With pyridine; thionyl chloride; at 60℃; for 9h;Reflux; To a stirredsolution of 3-Methylbenzene-1,2-diamine (15; 5 g , 41 mmol) in 20 mL of pyridine,thionyl chloride was added very slowly (8.2 mL, 110 mmol,2.7 eq.), while the temperature was kept at 60C. After that, theresulting slurry was heated to reflux for 9 h. The dark reaction mixturewas allowed to cool to room temperature and hydrolyzed with water verycarefully. After adding 1 L of water the mixture was steam distilled. Thedistillation was stopped, after 800 mL of steam; the aqueous phase wassaturated with NaCl and extracted four times with diethyl ether. Thecombined organic layers were dried over Na2SO4 andevaporated to dryness to afford the oily product (2.7 g, 13 mmol,44%). 1H-NMR (300 MHz, Acetone): δ = 7.81 (d, J = 8.8Hz, 1H), 7.59 - 7.49 (m, 1H), 7.41 (d, J = 6.7 Hz, 1H), 2.67 (s,3H) ppm. 13C-NMR (75 MHz, Acetone): δ = 156.15, 155.74,132.29, 130.63, 128.90, 119.58, 17.80 ppm. MS (EI): m/z = 150 [M+].EA calc. for C7H6N2S: C, 55.97; H, 4.03; N,18.65; found: C, 56.20; H, 4.13; N, 18.41.
With thionyl chloride; In pyridine; water; A. 4-Methyl-benzo[1,2,5]thiadiazole (839A) To a solution of 2,3-diaminotoluene (5.0 g, 40.9 mmol) in pyridine (40 mL) at 0 C. was added thionyl chloride (7.0 mL, 98.2 mmol) dropwise. The reaction mixture was stirred at 0 C. for 30 mins, then water (200 mL) was added. The solution was extracted with dicholomethane (2*250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839A (5.57 g) as a dark brown liquid.

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