4-Chlorophenyl Isocyanate → HCID 3958937, compound

Participants

Reaction Conditions

Reaction Steps

A solution of p-chlorophenyl isocyanate (15.3 g, 0.10 mol) in toluene (50 ml) is metered at room temperature into a solution of methyl anthranilate (15.1 g, 0.10 mol) in toluene (100 ml). After addition is complete, the mixture is stirred at 90° C. for 2 hours. Triethylamine (1.4 ml, 1.0 g, 0.010 mol) is metered in and the mixture is stirred at 90° C. for a further 3 hours. After cooling, the product is filtered off with suction and washed with 3×20 ml of toluene and dried. 21.0 g of 3-(4-chlorophenyl)-2,4(1H,3H)-quinazolinedione (yield: 77.0% of theory) of melting point 288° to 290° C. are obtained. According to thin-layer chromatography, the product is contaminated with the intermediate ethyl N-(4-chlorophenylcarbamoyl)anthranilate.

Provenance & Evidence