m-Chloroperbenzoic acid → Benzenesulfonamide, 4-hydroxy-N-(2-oxiranylmethyl)-N-(1-phenylethyl)-

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Reaction Steps

5 ml of chloroform solution containing 1 g (3.2 mmol) of N-allyl-N-α-methylbenzyl-4-hydroxybenzenesulfonamide was added to 30 ml of a chloroform solution of 828 mg (4.8 mmol) of metachloroperbenzoic acid, followed by refluxing for 2 hours. After completion of the reaction, the chloroform solution was washed with an aqueous sodium thiosulfate solution and then an aqueous sodium bicarbonate solution. After drying, the solvent was distilled off and the resulting crude product was purified by the silica gel column chromatography (hexane-ethyl acetate) to obtain 910 mg of N-(2,3-epoxypropyl)-N-α-methylbenzyl-4-hydroxybenzenesulfonamide (Compound No. 37). The melting point was found to be 82.0° to 86.0° C. The results of the elemental analysis are shown below.

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