Ethyl Acetate → HCID 7235814, compound

Participants

Reaction Steps

O-toluidine (Fluka; 0.118 mL, 1.1 mmol) was added to a clear light yellow solution of 4-cyano-benzenesulfonyl chloride (ABCR GmbH & Co. KG; 202 mg, 1 mmol) in pyridine (5 mL). The resulting clear red-brown solution was then stirred at room temperature for 18 hrs. Subsequently the reaction mixture was diluted with water (50 mL) and ethyl acetate (50 mL). The liquid layers were separated and the aqueous fraction was re-extracted twice with ethyl acetate (25 mL). The combined organic layers were washed with 0.1 M hydrochloric acid and brine (50 mL each), dried with sodium sulfate, filtered and evaporated under reduced pressure. The residue was dried under high vacuum to give 4-cyano-N-o-tolyl-benzenesulfonamide (314 mg, 0.92 mmol, 92% yield) as pale brown oil.

Provenance & Evidence