Water → HCID 18932302, compound

Participants

Reaction Steps

0.27 ml of methyl iodide were added to a solution of 138.6 mg of methyl N-[4-(benzothiazol-2-ylmethoxy)phenyl]carbamate (prepared as described in Example 11) in 5 ml of dimethylformamide cooled in an ice-water bath and then 19.4 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to the resulting mixture. The reaction mixture was stirred at the same temperature for 10 minutes, the temperature of the mixture was then elevated to room temperature and the mixture was stirred for a further 30 minutes. At the end of this time, water 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 was 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 2:1 by volume mixture of hexane and ethyl acetate to give 126.7 mg (yield 87%) of the title compound as a solid having a melting point of 85°-87° C.

Provenance & Evidence