Sodium hydride → Methyl N-[4-(6-methoxybenzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

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Reaction Steps

23 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 82 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 15 minutes, and then 150 mg of 2-bromomethyl-6-methoxybenzothiazole [prepared as described in Example 6(a) above] were added. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 6 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 with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 110 mg (yield 68%) of the title compound as a solid having a melting point of 123° to 125° C.

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