Hydrochloric Acid → N-[(Benzoylsulfanyl)acetyl]glycine

Participants

Reaction Steps

To a stirring solution under argon at 0° C. of (1.50g, 10mmoles) N-chloroacetylglycine in (25 mL) ethanol was added (1.41 ml, 12 mmoles) thiobenzoic acid, followed by (7.0 mL, 3N, 21 mmoles) potassium hydroxide over 3 minutes. The reaction was allowed to heat to room temperature for 20 minutes followed by reflux under argon at 50° C. for 2 hours. The reaction was cooled to room temperature and acidified with (5 mL, 2N) hydrochloric acid. The ethanol was rotavapped off to leave N-(S-benzoylmercaptoacetyl)-glycine (m.p. 140.5°-141.5° C.), a white solid, which was washed with water, filtered, and dried in vacuo (2.46g, 98% yield).

Provenance & Evidence