Methyl 3-amino-4-hydroxybenzoate → 2-Mercapto-1,3-benzoxazole-5-carboxylic acid methyl ester

Participants

Reaction Steps

Methyl 3-amino-4-hydroxybenzoate (5.09 g, 30.4 mmol) and potassium O-ethyl carbonodithioate (6.35 g, 39.6 mmol) were combined in pyridine (50 mL) and heated to reflux for two hours. The reaction mixture was cooled to ambient temperature. The mixture was filtered, washed with a 1 N aqueous hydrochloric acid solution, and dried on a vacuum filter overnight to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.88 (s, 3 H) 7.63 (d, J=8.48 Hz, 1 H) 7.69 (d, J=1.70 Hz, 1 H) 7.89 (dd, J=8.82, 1.70 Hz, 1 H); MS (ESI−) m/z 207.87 (M−H)−.

Provenance & Evidence