Methyl iodide → HCID 18932266, compound

Participants

Reaction Steps

15.1 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 102.0 mg of N-(benzothiazol-2-ylmethoxy)acetamide (prepared as described in Example 1) in 2 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred for 5 minutes, after which 0.023 ml of methyl iodide were added, the temperature of the resulting mixture was elevated to room temperature and the mixture was then 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 and the resulting residue was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate to give 106.8 mg (yield 100%) of the title compound as a solid having a melting point of 119° to 120° C.

Provenance & Evidence