Benzenesulfonamide, N,4-dimethyl- → Phenoxycarbonyl-4-methylbenzene sulfonamide

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Reaction Steps

Phenyl chloroformate (1.57 g, 0.01 mol) and N-methyl-4-methylbenzene sulfonamide (1.85 g, 0.01 mol) were diluted with 1,2-dichlorobenzene (15 ml) and refluxed for 40 hrs. The solvent was evaporated in vacuo and the residue diluted dichloromethane and the dichloromethane washed with water (2×), dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo gave N-methyl-N*-phenoxycarbonyl-4-methylbenzene sulfonamide mp 98–100° C. MS m/z 305. (M+ calcd for C15H15NO4S=305). H NMR (300 MHz, CDCl3) d 2.43 (s, 3, CH3), 2.45 (s, 3, NCH3), 6.95 (m, 2, aromatic), 7.18–7.35 (m, 5, aromatic), 7.88 (m, 5, aromatic).

Provenance & Evidence