4-(Methylsulfamoyl)benzoic acid → Benzenesulfonamide, 4-(hydroxymethyl)-N-methyl-

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Reaction Steps

At 0° C., borane-THF complex (66.8 mL, 1 M in THF) is carefully added to a solution of 4-methylsulfamoyl-benzoic acid (3.56 g, 16.5 mmol) in THF (90 mL). The mixture is refluxed for 1.5 h, cooled to rt and diluted with 1 N aq. HCl (175 mL). The mixture is extracted with EA and the organic extract is washed with sat. aq. NaHCO3, dried over MgSO4 and filtered. The filtrate is concentrated and the crude product is purified by CC on silica gel eluting with DCM containing 5% of methanol to give 4-hydroxymethyl-N-methyl-benzenesulfonamide (1.61 g) as a colourless oil; LC-MS: tR=0.56 min, [M+1+CH3CN]+=243.14.

Provenance & Evidence