Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

Participants

Reaction Steps

Dimethylformamide (0.5 ml) was added to a suspension of 7-(benzyloxy)quinazolin-4-(3H)-one (5.04 g, 20 mmol) in thionyl chloride (50 ml) and the mixture heated at reflux for 2 hours. The thionyl chloride was removed in vacuo and the residual oil dissolved in dichloromethane (100 ml). This solution was slowly added to an aqueous saturated solution of sodium bicarbonate (100 ml) and the organic phase recovered. The aqueous phase was extracted with dichloromethane (2×50 ml) and the combined organics dried and concentrated to yield 7-(benzyloxy)-4-chloroquinazoline (4.68 g, 86.5% yield):

Provenance & Evidence