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[ CAS No. 17583-10-7 ] {[proInfo.proName]}

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Chemical Structure| 17583-10-7
Chemical Structure| 17583-10-7
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Product Details of [ 17583-10-7 ]

CAS No. :17583-10-7 MDL No. :MFCD00460519
Formula : C7H8N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :JAZOMJIYYHHUBH-UHFFFAOYSA-N
M.W : 168.22 Pubchem ID :587850
Synonyms :

Safety of [ 17583-10-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17583-10-7 ]

* 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 [ 17583-10-7 ]

[ 17583-10-7 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 60060-44-8 ]
  • [ 17356-08-0 ]
  • [ 17583-10-7 ]
YieldReaction ConditionsOperation in experiment
91% With pyridine; In methanol; for 4h;Reflux; Step-ii: 2-amino-5,6-dihydrobenzo[dlthiazol-7(4H)-one To a 100 mL round bottom flask, were added 2-bromocyclohexane- 1,3-dione ( 1.0 g, 5.23 mmol) and methanol (15 mL). To the same flask, thiourea (0.0.397 g, 5.23 mmol) and pyridine (0.412 g, 5.23 mmol) were added. The reaction mixture was stirred at reflux temperature for 4 h. The volatiles were evaporated under reduced pressure to get residue. The residue was dissolved in water and stirred for 5 min. to get precipitate. The precipitate was collected by filtration and washed with water to get the title compound [0.8 g, 91 percent]. H NMR (300 MHz, DMSO-de): delta 8.12 (brs, 2H), 2.69 (t, 2H), 2.38 (t, 2H), 2.02 (m, 2H); LC-MS (ESI): 168.9 [M+H]+.
47% 2-Amino-S, 6-dihydro-4H-benzothiazol-7-one A solution of 2-bromo-cyclohexane-1, 3-dione (1.0 g, 5.2 mmol) and thiourea (0.4 g, 5.2 mmol) in anhydrous ETOH (7 mL) was heated under reflux for 3 h. The reaction mixture was cooled, concentrated under vacuum, and washed with Et2O (20 mL). The residue was dissolved in H20 (10 mL) and 6 M aq NH40H (4 mL) was added dropwise. The yellow precipitate was collected, dried, and crystallised from ETOH to afford the titl compound as yellow crystals (0.41 g, 47 percent)
42% In ethanol;Reflux; Step 2; To a suspension of thiourea (3.8 g) in ethanol (100 mL), 74 (9.5 g, 50 mmol) was added. The suspension was then stirred under reflux overnight. The reaction mixture was cooled, filtered, and then washed sequentially with water and ethanol to yield 75 as a yellow solid (3.1 g, y. 42percent). 1H-NMR (300 Mz) (DMSO): 1.99-2.05 (m, 2H), 2.39 (t, J = 5.5 Hz, 2H), 2.70 (t, J = 6 Hz, 2H), 8.55-8.66 (m, 2H).
With bromine; In ethanol; at 20℃; for 2h;Heating / reflux; Synthesis of Intermediate Compound (IV) 112 g (1.0 mol) 1,3-cyclohexanedione are suspended in 700 mL ice water and 51.6 mL (1.0 mol) bromine are added dropwise at 0° C. within 45 minutes. The suspension is stirred for 3.5 hours at max. 10° C. Then it is suction filtered and the solid is stirred in 800 mL water, suction filtered, washed with 3 L water and dried. The solid obtained is recrystallised from ethanol. Yield: 37 g (m.p.: 159-160° C.) 15.5 g (0.2 mol) thiourea are placed in 200 mL ethanol at ambient temperature. To this suspension are added batchwise 37.1 g (0.2 mol) of the intermediate described above, then the mixture is rinsed with 60 mL ethanol. The solution that gradually forms is refluxed for 2 hours with stirring and then evaporated down. The residue is extracted with water and diethyl ether, the aqueous phase is made basic with sodium carbonate solution. The resulting solid is suction filtered, washed with water, then stirred with methanol and evaporated to dryness. Yield: 22 g (m.p.: 265-268° C.) 230 mL (2.4 mol) acetic anhydride are placed at ambient temperature, 22 g (0.13 mol) of the intermediate described above are added and the mixture is refluxed for 3 hours with stirring. The suspension goes partly into solution. After cooling with ice/common salt bath the solid is solid suction filtered, decocted 2.x. in 150 mL acetone, suction filtered and dried. Yield: 25 g (m.p.: 268-272° C.) of the intermediate compound (IV)
With sodium hydrogencarbonate; In ethanol; at 80℃; for 4h; General procedure: To a solutionof bromoketones (22a or 22b) (10.3 mmol, 1.0 equiv) inethanol (50 mL) was added thiourea (10.3 mmol, 1.0 equiv) andsodium bicarbonate (10.3 mmol, 1.0 equiv). The resulting mixturewas stirred at 80 C for 4 h and then cooled to room temperature,and the solid was filtered off. The filtrate was evaporated underreduced pressure to afford crude residue, which was crystallized inethanol to obtain the desired product. 2-Amino-5,6-dihydrobenzo[d]thiazol-7(4H)-one (23a). This titlecompound was prepared from 22a following step 2 of generalprocedure E. Pale solid (38.3percent), mp 249e250 C. 1H NMR (300 MHz,DMSO-d6) d 8.16e8.07 (m, 2H), 2.72e2.63 (m, 2H), 2.39e2.32 (m,2H), 2.04e1.93 (m, 2H). MS (ESI) m/z: 166.9 [M-H]-.

  • 2
  • [ 108-24-7 ]
  • [ 17583-10-7 ]
  • N-<(4,5,6,7-tetrahydro-7-oxo)benzothiazol-2-yl>acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% for 5h;Reflux; Step 3; Acetic anhydride (5 mL) was added to 75 (500 mg, 3.5 mmol). After stirring under reflux for 5 hours, the reaction mixture was cooled and then filtered to yield 76 as a brown solid (360 mg, y. 60percent). 1H-NMR (300 Mz) (DMSO): 2.05-2.09 (m, 2H), 2.49 (m, 5H), 2.85 (t, J = 6.5 Hz, 2H), 12.56 (s, 1H).
at 20℃; for 3h;Heating / reflux; Synthesis of Intermediate Compound (IV) 112 g (1.0 mol) 1,3-cyclohexanedione are suspended in 700 mL ice water and 51.6 mL (1.0 mol) bromine are added dropwise at 0° C. within 45 minutes. The suspension is stirred for 3.5 hours at max. 10° C. Then it is suction filtered and the solid is stirred in 800 mL water, suction filtered, washed with 3 L water and dried. The solid obtained is recrystallised from ethanol. Yield: 37 g (m.p.: 159-160° C.) 15.5 g (0.2 mol) thiourea are placed in 200 mL ethanol at ambient temperature. To this suspension are added batchwise 37.1 g (0.2 mol) of the intermediate described above, then the mixture is rinsed with 60 mL ethanol. The solution that gradually forms is refluxed for 2 hours with stirring and then evaporated down. The residue is extracted with water and diethyl ether, the aqueous phase is made basic with sodium carbonate solution. The resulting solid is suction filtered, washed with water, then stirred with methanol and evaporated to dryness. Yield: 22 g (m.p.: 265-268° C.) 230 mL (2.4 mol) acetic anhydride are placed at ambient temperature, 22 g (0.13 mol) of the intermediate described above are added and the mixture is refluxed for 3 hours with stirring. The suspension goes partly into solution. After cooling with ice/common salt bath the solid is solid suction filtered, decocted 2.x. in 150 mL acetone, suction filtered and dried. Yield: 25 g (m.p.: 268-272° C.) of the intermediate compound (IV)
at 20℃; for 19.75h;Reflux; Stage A.5: N-(7-Oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamideTo acetic anhydride (80 mL) was added at rt <strong>[17583-10-7]2-amino-5,6-dihydro-4H-benzothiazol-7-one</strong> (10 g, 59.4 mmol) and the resulting suspension was heated to reflux. After 1.75 h stirring at reflux, the RM was allowed to cool with stirring and stirred for 18 h at it before further cooling with an ice/NaCl bath, and a solid was collected by filtration. The solid was then triturated twice with refluxing acetone (10 mL then 15 mL) before filtering and drying under vacuum at 40° C. to give the title product as a beige solid. HPLC: tR 3.47 min (method D). MS: M-H=211.1. 1H-NMR in DMSO-d6 (600 MHz): 12.55 (s, br, 1H); 2.84 (t, 2H); 2.48 (t, 2H); 2.17 (s, 3H); 2.065 (qt, 2H).
at 20℃; for 3h;Heating / reflux; 230 mL (2.4 mol) acetic anhydride are placed at ambient temperature, 22 g (0.13 mol) of the intermediate described above are added and the mixture is refluxed for 3 hours with stirring. The suspension goes partly into solution. After cooling with ice/saline bath the solid is suction filtered, decocted 2.x. in 150 mL acetone, suction filtered and dried. Yield: 25 g (m.p.: 268-272° C.)

  • 3
  • [ 17356-08-0 ]
  • dimethyl (1,2-epoxy-3-oxo-cyclohex-1-yl)phosphonate [ No CAS ]
  • [ 17583-10-7 ]
  • 4
  • [ 17583-10-7 ]
  • [ 155778-36-2 ]
YieldReaction ConditionsOperation in experiment
83% With sodium azide; sulfuric acid; In chloroform; at 20℃; for 50h; To a stirred solution of <strong>[17583-10-7]2-amino-5,6-dihydro-4H-benzothiazol-7-one</strong> (10 g, 59 mmol) in chloroform (250 mL) was added concentrated H2S04 at room temperature. Sodium azide (7.6 g, 117 mmol) was then carefully added to the mixture over two hours (vigorous gas evolution). The reaction mixture was further stirred at room temperature for 48 hours. The mixture was poured into crushed ice and a saturated solution of NaHCC"3 was added until the pH of the solution was about 9. The formed precipitate was filtered off and washed with H20 and AcOEt. The solid was dried in the oven (T = 50°C) to yield 9 g (83percent) of intermediate 5 that was used in the next step without further purification.
With sodium azide; sulfuric acid; In chloroform; at 20℃; for 50h; To a stirred solution of <strong>[17583-10-7]2-amino-5,6-dihydro-4H-benzothiazol-7-one</strong> (10 g, 59 mmol) in chloroform (250 mL) was added concentrated H2SO4 at room temperature. Sodium azide (7.6 g, 117 mmol) was then carefully added to the mixture over two hours (vigorous gas evolution). The reaction mixture was further stirred at room temperature for 48 hours. The mixture was poured into crushed ice and a saturated solution of NaHCO3 was added until the pH of the solution was about 9. The formed precipitate was filtered off and washed with H2O and AcOEt. The solid was dried in the oven (T=50° C.) to yield 9 g (83percent) of intermediate 5 that was used in the next step without further purification.
  • 5
  • [ 17583-10-7 ]
  • [ 330203-55-9 ]
  • 6
  • [ 2941-64-2 ]
  • [ 17583-10-7 ]
  • [ 883864-80-0 ]
YieldReaction ConditionsOperation in experiment
71% Synthesis of Intermediate Compound (VlI.1) According to Diagram 1 60.73 g (361 mmol) <strong>[17583-10-7]2-amino-5,6-dihydro-4H-benzothiazol-7-one</strong> are placed in 400 ml of tetrahydrofuran, 68.02 ml (397 mmol) diisopropylethylamine and 0.100 g dimethylaminopyridine are added. While cooling with ice the mixture is combined with 46.88 g (361 mmol) ethylchlorothioformate. It is refluxed for 3 hours with stirring, then 0.05 eq diisopropylethylamine are added. After a further 3.5 hours at reflux temperature and 16 hours at ambient temperature a total of 0.15 eq diisopropylethylamine are added. The reaction mixture is added to water, stirred for 16 hours, cooled to 0° C. and suction filtered. The precipitate is stirred with petroleum ether. Yield: 65.60 g (71percent of theoretical) of the intermediate compound (VIl.1)
  • 7
  • [ 17583-10-7 ]
  • 2-phenylamino-4,5,6,7-tetrahydrobenzothiazol-7-one [ No CAS ]
  • 8
  • [ 17583-10-7 ]
  • 2-(morpholin-4-yl)-4,5,6,7-tetrahydrobenzothiazol-7-one [ No CAS ]
  • 9
  • [ 17583-10-7 ]
  • 2-piperidino-4,5,6,7-tetrahydrobenzothiazol-7-one [ No CAS ]
  • 10
  • [ 17583-10-7 ]
  • [ 17583-11-8 ]
  • 11
  • [ 4637-24-5 ]
  • [ 17583-10-7 ]
  • [ 827598-61-8 ]
YieldReaction ConditionsOperation in experiment
59% In ethanol; at 150℃; for 0.5h;Irradiation; N'-(6-Dimethylaminomethylene-7-oxo-4,5, 6, 7-tetrahydro-benzothiazol-2-yl)-N, N-dimethyl- formamidine A mixture of 2-amino-5, 6-dihydro-4H-benzothiazol-7-one (0.5 g, 3 mmol) and N, N- dimethylformamide dimethyl acetal (1.96 mL, 1. 76 g, 14.8 mmol) in ETOH (2mL) was heated under microwave irradiation (300 W, 150 °C) for 30 min. The mixture was concentrated under vacuum before purification by flash column chromatography (50 percent EtOAc: hexane) to afford the title product as a tan solid (0.49 g, 59 percent)
  • 12
  • [ 90-27-7 ]
  • [ 17583-10-7 ]
  • N-(7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-2-phenyl-butyramide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With triethylamine; HATU; In DMF (N,N-dimethyl-formamide); for 16h; 2-Amino-5,6-dihydro-4H-benzothiazol-7-one (34 mg, 0.20 mmol) and 2-phenyl-butyric acid (33 mg, 0.20 mmol) were dissolved in N, N-DIMETHYLFORMAMIDE (1 mL) containing triethylamine (84.1 L, 0.600 mmol). 0- (7- AZABENZOTRIAZOL-L-YL)-N, N, N , N -TETRAMETHYLURONIUM hexafluorophosphate (84 mg, 0.22 mmol) was added and the solution was allowed to stir for 16 hours. The crude product was purified by reverse-phase preparative liquid chromatography (31 mg, 0.099 mmol, 49 percent). ESI-MS m/z calc. 314.1, found 315.3 (M+1) + Retention time 2.90 minutes.
  • 13
  • [ 109-90-0 ]
  • [ 17583-10-7 ]
  • [ 352529-86-3 ]
YieldReaction ConditionsOperation in experiment
13.97 g (85%) With triethylamine; In diethyl ether; N,N-dimethyl-formamide; Preparation 6 1-(7-Oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea (4). A solution of <strong>[17583-10-7]2-amino-7-oxo-4,5,6,7-tetrahydro-benzothiazole</strong> 3 (11.56 g, 68.7 mmol) in anhydrous DMF (200 mL) was treated with triethylamine (19.2 mL, 137 mmol, 2.0 eq) and ethyl isocyanate (10.9 mL, 137 mmol, 2.0 eq). The reaction mixture was heated at about 90° C. with stirring for about 3 hours. The DMF solvent was distilled off under reduced pressure. A sticky brown residue was obtained. Treatment with Et2O (100 mL) gave a precipitate, which was filtered off and washed with more Et2O (50 mL). The light brown colored solid was dried under vacuum to give 13.97 g (85percent) of 4. The material was used in the following synthesis without further purification. 1H NMR (DMSO)gamma 10.95 (br s, 1H, NH), 6.66 (br s, I H, NH), 3.16 (p, 2H, J=7.2 Hz, CH2), 2.79 (t, 2H, J=6.1 Hz, CH2), 2.45 (t, 2H, J=6.5 Hz, CH2), 2.05 (p, 2H, J=6.4 Hz, CH2), 1.07 (t, 3H, J=7.2 Hz, CH3); LC/MS 240 (MH+); RP-HPLC RT 2.27 minutes.
  • 14
  • [ 60060-44-8 ]
  • [ 17583-10-7 ]
YieldReaction ConditionsOperation in experiment
With thiourea; In tetrahydrofuran; 1,4-dioxane; water; Preparation 5 2-Amino-7-oxo-4,5,6,7-tetrahydro-benzothiazole (3). A suspension of 2-bromo-1,3-cyclohexadione 1 (15.44 g, 80.8 mmol) and thiourea (6.15 g, 80.8 mmol, 1.0 eq) in anhydrous THF (120 mL) was stirred at about 20° C. for about 2 days. The disappearance of 1 and the appearance of 2 could be seen on TLC. The mixture was concentrated and anhydrous dioxane (120 mL) was added. The reaction mixture was heated at about 110° C. for about 1 day. It was cooled down and the precipitation was filtered off and washed with THF (2*150 mL). The solid was dissolved in H2O (100 mL) and neutralized with sat. NaHCO3 solution whereupon a precipitate formed. The precipitate was collected and recrystallized from MeOH to give 7.93 g (58percent) of 3.1H NMR (DMSO)gamma 8.10 (br s, 2H, NH2), 2.67 (t, 2H, J=6.0 Hz, CH2), 2.36 (t, 2H, J 6.0 Hz, CH2), 1.99 (p, 2H, J=6.4 Hz, CH2); Mp 259.3-262.5° C. (Decomposed).
YieldReaction ConditionsOperation in experiment
68% (A) 2-Amino-4,5-dihydrobenzothiazole-7(6H)-one 2-Bromo-1,3-cyclohexadione (30 g) prepared in Route 1 (A) was suspended into absolute ethanol, and thiourea (13) was added thereto. The reaction mixture was heated to reflux for 12-15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to evaporate the solvent. Acetone (70 ml) was added to the residue to give solids, which were filtered, washed with acetone (30 ml) and dried to give hydrobromide of the titled compound (27 g, 71percent). The hydrobromide was neutralized with sodium hydroxide solution to give the titled compound (18 g, 68percent)
  • 16
  • [ 70-11-1 ]
  • 2-Phenyl-5,6-dihydroimidazo[2,1-b]benzothiazole-8(7H)-one [ No CAS ]
  • [ 17583-10-7 ]
YieldReaction ConditionsOperation in experiment
76% In N-methyl-acetamide; (B) 2-Phenyl-5,6-dihydroimidazo[2,1-b]benzothiazole-8(7H)-one 2-Amino-4,5-dihydrobenzothiazole-7(6H)-one (18 g) prepared in the above (A) was dissolved into dimethylformamide (250 ml), and 2-bromoacetophenone (21,83 g) was added thereto followed by heating to reflux for 12-15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and placed into distilled water. The resulting precipitates were filtered, neutralized with sodium hydroxide solution, filtered, washed with ethyl acetate (100 ml), and dried to give the titled compound (21.25 g, 76percent).
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