Dimethylformamide → 4-Chloro-2-phenylquinazoline

Participants

Reaction Steps

To a mixture of 20.8 g of 2-phenylquinazolin-4(3H)-one and 195 ml of thionyl chloride was slowly added 6.85 g of dimethylformamide and the mixture was heated under reflux for 75 minutes. The mixture was poured into 1000 ml of ice and the ice allowed to melt. The precipitate was collected by filtration to give a tan solid, m.p. 135°. The still-moist solid was dissolved in methylene chloride, the solution was dried over magnesium sulfate and was filtered. The filtrate was evaporated to dryness and the residue recrystallized from hexane to give 10.45 g of 4-chloro-2-phenylquinazoline which melted at 127°-128.5°.

Provenance & Evidence