Hydrochloric Acid → 4-Hydrazino-N-methylbenzenemethanesulfonamide hydrochloride

Participants

Reaction Steps

A solution of sodium nitrite (13.72 g) in water (160 ml) was added slowly to a cooled stirred mixture of 4-Amino-N-methylbenzene methanesulphonamide (39.3 g), water (240 ml) and conc. hydrochloric acid (400 ml) such that the temperature did not exceed 0°. After stirring for 15 min this mixture was added slowly to a cold solution of stannous chloride dihydrate (221.1 g) in conc. hydrochloric acid (400 ml) again keeping the temperature below 0°. Once the addition was complete the mixture was allowed to warm to room temperature (1 h). The solid was collected by filtration, washed well with diethyl ether (4×250 ml) and dried at 45° to give the title compound as a white powder (31.6 g). An assay by periodate titration showed this to be 91.3% pure.

Provenance & Evidence