HCID 19875682, compound → HCID 19875683, compound
Reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]([CH3:17])[N:13]=[N:14][C:15]=2[SH:16])[CH:8]=[CH:9][CH:10]=1)(=O)C>Cl>[NH2:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]([CH3:17])[N:13]=[N:14][C:15]=2[SH:16])[CH:8]=[CH:9][CH:10]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
150 ml of 12N hydrochloric acid was added to 10 g of 4-(3-acetylaminophenyl)-3-methyl-5-mercaptotriazole (4) thus obtained. The system was then heated under reflux. After 3 hours, the system was cooled. Water was then distilled off by a rotary evaporator to obtain crystals of crude 4-(3-aminophenyl)-3-methyl-5-mercaptotriazole (5). 100 ml of acetonitrile was added to this crystal. 12 g of pyridine was then added to the system. The system was stirred. 7.5 g of phenyl chlorocarbonate was added dropwise to the system while the system was kept at a temperature of 5° C. or lower in an iced-water bath. After completion of the dropwise addition, the system was allowed to undergo reaction over 10 minutes. 20 ml of water was added to the reaction solution. The solvent was then distilled off by a rotary evaporator. The resulting concentrated solution was extracted with ethyl acetate. The extract was then washed with saturated aqueous solution of sodium chloride, and dried with sodium sulfate anhydride. The solvent was distilled off to obtain a crystals of crude 4-(3-phenoxycarbonylaminophenyl)-3-methyl-5-mercaptotriazole (6). The crude crystals were recrystallized from ethyl acetate to obtain 13 g of Compound (6). (Yield: 98%; m.p. 188° C.)
Workup
- customthus obtained
- temperatureThe system was then heated
- temperatureunder reflux
- temperaturethe system was cooled
- distillationWater was then distilled off by a rotary evaporator
Sources & evidence
- ORD record
- ord-fd0da5ff47974d9fbb46798017057b77
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05151357
Reaction notes
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