When orthophenylene diamine interacts with chloroacetyl chloride, does it produce quinazoline or benzimidazole ??

26 January 2021 1 628 Report

The primary product of this reaction is mono-chloroacetate of o-phenylenediamine (plus N,N'-bis-chloroacetate, ratio depending on stoichiometry). After that, the mono-chloroacetate may cyclise to either 1,2,3,4-tetrahydroquinoxaline-2-one (6-member ring formation) or 2-chloromethyl-1H-benzimidazole (5-member ring formation).

I don't see how quinazoline structure can be produced in this reaction.

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