Methanesulfonyl chloride → N-mesyl-O-(p-methoxybenzyl)hydroxylamine

Participants

Reaction Steps

63.0 g (0.55 mole) of mesyl chloride was added dropwise to a solution of 76.5 g (0.5 mole) of O-(p-methoxybenzyl)-hydroxylamine in 400 ml of pyridine while ice-cooling and stirring. After completion of the addition, the resulting mixture was stirred at room temperature (about 20°-30° C) for 5 hours and then the solvent was removed by distillation. 600 ml of ethyl acetate was added to the resulting residue, and the mixture was washed successively with 1N hydrochloric acid and water. The mixture was then dried and the solvent was distilled off to obtain 75 g (64.8% yield) of N-mesyl-O-(p-methoxybenzyl)hydroxylamine (IV) having a melting point of 114°-116° C.

Provenance & Evidence