Sodium hydride → Methyl N-[4-(benzothiazol-2-ylmethylthio)phenyl]carbamate

Participants

Reaction Steps

100.5 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 418.5 mg of methyl N-(4-mercaptophenyl)carbamate [prepared as described in step (a) above] in 8.4 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 10 minutes, and then 573.1 mg of 2-bromomethylbenzothiazole were added. The temperature of the reaction mixture was then elevated to room temperature and the mixture was stirred for 3.5 hours. At the end of this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 462.7 mg (yield 81%) of the title compound as a solid having a melting point of 139° to 141° C.

Provenance & Evidence