Hydrochloric Acid → 3-(5-Cyano-pyridin-2-ylsulfanyl)-benzoic acid

Participants

Reaction Conditions

Reaction Steps

Add sodium hydride (60% dispersion in mineral oil, 635 mg, 15.88 mmol) to a solution of 3-mercapto-benzoic acid (1.11 g, 7.22 mmol) in dimethylformamide (50 mL) chilled to 0° C. and stir. After 10 minutes add 6-chloro-nicotinonitrile (1.00 g, 7.22 mmol). Warm gradually to ambient temperature. After 18 hours, add 1N aqueous hydrochloric acid (200 mL). Filter resulting precipitate, washing with water and hexanes to yield the title compound as a tan solid (1.25 g, 68%): 1H NMR (DMSO-d6) δ 7.22 (d, 1H), 7.67 (t, 1H), 7.88 (dt, 1H), 8.07-8.12 (m, 3H), 8.82 (dd, 1H), 13.30 (bs, 1H).

Provenance & Evidence