Sodium hydride → Methyl N-[4-(5-fluorobenzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

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Reaction Steps

54.6 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 204.9 mg of methyl N-(4-hydroxy-2-methylphenyl)carbamate [prepared as described in Example 15(a) above] in 5 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 5 minutes, and then 366.2 mg of 2-bromomethyl-5-fluorobenzothiazole [prepared as described in step (a) above] were added. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 1.5 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 3:1 by volume mixture of hexane and ethyl acetate as the eluent to give 263.3 mg (yield 65%) of the title compound as a solid having a melting point of 165° to 168° C.

Provenance & Evidence