Thionyl Chloride → 2-(4-Tert-butylphenyl)-4-chloroquinazoline

Participants

Reaction Steps

A mixture of 8.9 g of 2-(4-tert-butylphenyl)quinazolin-4(3H)-one and 60 ml of thionyl chloride was treated with 2.34 g of dimethylformamide as described in Example VI. The initial solid was triturated with cyclohexane, filtered, and the filtrate concentrated to give an oil which solidified on standing to give a solid, m.p. 74°-77°. This solid was recrystallized twice from petroleum ether (30°-60° fraction) using a low-temperature recrystallization apparatus to give 6.3 g of 4-chloro-2-(4-tert-butylphenyl)quinazoline, m.p. 75°-76.5°; ir and nmr spectra were consistent with the assigned structure.

Provenance & Evidence