Phosphorus oxychloride → 4-Chloroquinazoline

Participants

Reaction Steps

Phosphorus oxychloride (64 mL, 687 mmol) and phosphorus pentachloride (14.89 g, 71.50 mmol) were added to 4-hydroxyquinazoline (7.94 g, 52.3 mmol), and the solution was stirred for 20 minutes under reflux. The reaction mixture was evaporated in vacuo, and the residue was dissolved in chloroform. The chloroform solution was poured on an ice bath, concentrated aqueous ammonia was added to adjust the pH to 10, then, the solution was partitioned. The aqueous layer was extracted with chloroform, and the combined chloroform layers were washed with water. The organic layer was dried over anhydrous magnesium sulfate, then, evaporated in vacuo, and the title compound (8.03 g,48.8 mmol, 93%) was obtained. This was used in the next reaction without purification.

Provenance & Evidence