55305-43-6

N-Cyano-N-phenyl-p-toluenesulfonamide is a useful research reactant for the synthesis of synthesis of 1,?2,?4-?triazol-?3-?imines through stepwise cycloaddition.

In a dry 250 mL Schlenk flask, phenylurea (10.9 g, 80 mmol) was dissolved in pyridine (54 mL). The flask was placed in a room temperature water bath and stirred. Tosyl chloride (52.8 g, 277 mmol) was added slowly over 5 minutes. The reaction mixture was continued to be stirred for 20 minutes and then slowly poured into ice-cooled water (400 mL) under mechanical stirring. The precipitate formed during mechanical stirring was filtered and washed with plenty of water. The crude product was treated with ethanol (50 mL) and recrystallized from the same solvent. The precipitate was purified by column chromatography using heptane: ethyl acetate (15:1) as eluent to afford N-cyano-4-methyl-N-phenylbenzenesulfonamide as a colorless solid (16.5 g, 76% yield).

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