Methylamine → 4-bromo-N-methylbenzene-1-sulfonamide

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Reaction Steps

4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and methylamine (10 mL, 33% in ethanol) were stirred in a sealed tube for 16 hours. The reaction mixture was concentrated in vacuo onto the Celite® reagent. The crude product was purified via Isco chromatography (the Redisep™ column, silica, gradient 0-3% ethyl acetate-dichloromethane) to provide 4-bromo-N-methylbenzenesulfonamide (0.11 g, 28%). MS (ESI) m/z 250. High performance liquid chromatography (HPLC) purity 100.0% at 210-370 nm, 7.4 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/Acetonitrile (ACN)+MeOH) for 10 min., hold 4 min.

Provenance & Evidence