Sulfisoxazole → 4-Benzylamino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (1.0 g, 3.74 mmol) and sodium bicarbonate (310 mg, 4.48 mmol) suspended in ethanol was added benzyl bromide (770 mg, 4.48 mmol). After 10 min of stirring at 70° C., the mixture became homogeneous. The reaction was stirred at 70° C. for 2 h and the solvent and volatiles were evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with brine (2×25 ml). After drying over magnesium sulfate, evaporation of the solvent left a viscous yellow oil which was chromatographed on silica gel to give 960 mg (72% yield) clear, colorless oil. Further purification by HPLC gave a white solid, m.p. 47°-8° C.

Provenance & Evidence