Thionyl Chloride → 4-Chloro-2-(4-methylphenyl)quinazoline

Participants

Reaction Steps

To a mixture of 7 g of 2-(4-methylphenyl)quinazolin-4(3H)-one and 50 ml of thionyl chloride was slowly added 2.16 g of dimethylformamide and the mixture was heated under reflux for 75 minutes. The mixture was poured into 250 ml of ice and the ice allowed to melt. The precipitate was collected to give 6.7 g of 4-chloro-2-(4-methylphenyl)quinazoline which melted at 113°-115° after recrystallization from petroleum ether (30°-60° fraction); ir and nmr spectra were consistent with the assigned structure. Calcd. for C15H11ClN2 : C, 70.73; H, 4.35; N, 11.00. Found: C, 70.92; H, 4.39; N, 11.09.

Provenance & Evidence