Benzoyl chloride → HCID 12478920, compound

Participants

Reaction Conditions

Reaction Steps

70.3 g of benzoyl chloride and 40 g of 50% strength aqueous sodium hydroxide solution are added simultaneously via 2 feed apparatuses in the course of 40 minutes at from 23° to 42° C. to a stirred mixture of 85.8 g of finely divided 6-chloroanthranilic acid, 0.9 g of trimethylbenzylammonium chloride and 1,250 g of 1,2-dichloroethane. Stirring is continued for 90 minutes at 28° C., the mixture is refluxed for 1 hour with separation of water, and 63.1 parts of thionyl chloride are added in the course of 45 minutes at 70° C., while stirring. Stirring is continued for 90 minutes at 82° C., after which the mixture is cooled to 40° C., extracted 3 times with water and evaporated down under reduced pressure, in the final stage at 140° C. under 20 mbar, to give 126.2 g (98%) of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one of melting point 151°-153° C. Comparison with a purified standard using HPLC shows that the purity is 96%.

Provenance & Evidence