Hydrochloric Acid → N-Butyl-p-toluenesulfonamide

Participants

Reaction Conditions

Reaction Steps

Dissolve butylamine (10 mmol) in methylene chloride (50 mL) and 10% sodium hydroxide (50 mL). Cool to 0° C. Add excess p-toluenesulfonyl chloride with stirring. After 1 hour allow the reaction to warm to room temperature and stir for 2 days. Neutralize the reaction with 0.5N hydrochloric acid and extract the aqueous with methylene chloride (2×100 mL). Rinse the combined organic extracts with water (100 mL), brine (100 mL), dry over anhydrous sodium sulfate, filter and concentrate under vacuum to provide N-butyl-4-methyl-benzenesulfonamide.

Provenance & Evidence