Phosphorus oxychloride → 7-(Benzylthio)-4-chloroquinazoline

Participants

Reaction Steps

A flask was charged with 7-(benzylthio)quinazolin-4(3H)-one (5.0 g, 18.63 mmol) and DCE (93 ml). POCl3 (5.21 ml, 55.9 mmol) was added, followed by Hunig's base (16.27 ml, 93 mmol). The flask was fitted with a reflux condensor, and the reaction was for two hours at 90° C. The reaction was washed with water and the layers were separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-75% EtOAc:Heptane) to afford 7-(benzylthio)-4-chloroquinazoline as a light yellow solid. (ESI) 287.0 (M+H)+.

Provenance & Evidence