Methylamine → N-Methyl-3-nitrobenzenesulfonamide

Participants

Reaction Steps

A reaction vessel charged with 3-nitro-benzenesulfonyl chloride (the compound of formula (U), 4.42 g, 20.0 mmol) in 150 mL of dry THF at 0° C. was further charged with methylamine (25.0 mL of a 2M solution in THF, 50 mmol, represented by the formula HNRR′ wherein R═H and R′=methyl). The resulting cloudy solution was stirred overnight at ambient temperature. The reaction mixture was then diluted with 150 mL of saturated sodium chloride solution and 50 mL of ethyl acetate. The layers were separated and the aqueous phase was extracted twice with 50 mL of ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, concentrated under reduced pressure. The resulting crude material was purified by recrystallization from ethanol to yield 4.20 g (19.5 mmol) of N-methyl-3-nitrobenzenesulfonamide, the compound of formula (V) wherein R is methyl.

Provenance & Evidence