Methanol → HCID 178503459, compound

Participants

Reaction Steps

To a solution of 2-(2-chlorobenzoyl)-3-ethoxyacrylic acid, ethyl ester (23.9 g, 23.9 mmol) in absolute ethanol (80 mL) was added thiourea (7.14 g, 23.9 mmol), followed by a solution of 25% sodium methoxide in methanol (20.4 mL, 89.3 mmol). The reaction mixture was heated to reflux for four hours, and then stirred at room temperature over night. The resulting mixture was diluted with water (50 mL) and then treated with iodomethane (11.99 mL, 21.5 mmol). The material was warmed to 40° C. and stirred for three hours. Water (10 mL) was added and the material allowed to cool to room temperature over 10 minutes. Another 50 mL of water was added and the product slowly crystallized out of the resulting solution. The product was collected by filtration (18.72 g, (M+H)+=281).

Provenance & Evidence