Methylamine → 4-Methoxy-N-methylbenzenesulfonamide

Participants

Reaction Steps

Part A: To a mixture of 50 mL of tetrahydrofuran, 15 mL (108 mmol) of triethylamine and 10 mL (116 mmol) of a 40% aqueous methylamine solution at 0 C, was added 15.0 g (72.6 mmol) of 4-methoxy-benzenesulfonyl chloride over a 15 minutes. After 1 hour, the solvents were removed in vacuo, 5% aqueous KHSO4 and ethyl acetate added, the organic layer separated, washed with saturated aqueous sodium bicarbonate, brine, dried with sodium sulfate, filtered and stripped to afford a white solid. This was recrystallized from hot ethyl acetate/hexane to afford 13.4 g of N-methyl-4-methoxybenzenesulfonamide, m/e=202 (M+H).

Provenance & Evidence