Synthesis of 1,3‐dihydro‐2 H ‐benzimidazol‐2‐one from 2‐aminobenzamide | Zendy

Heyman Duane A. | Zendy

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Synthesis of 1,3‐dihydro‐2 H ‐benzimidazol‐2‐one from 2‐aminobenzamide

Author(s) -

Heyman Duane A.

Publication year - 1978

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570150410

Subject(s) - chemistry , phthalic anhydride , yield (engineering) , hydrolysis , phthalic acid , organic chemistry , medicinal chemistry , catalysis , composite material , materials science

A method for the synthesis of 2‐henzimidazolone ( 1 ) has been devised which does not depend on 1,2‐diaminobenzene ( 2 ) as a starting material. This method produces 1 in good yield by the reaction of hypohalite with 2′‐carbamoylphthalanilic acid ( 7 ), a compound readily prepared by the reaction of 2‐aminobenzamide ( 3 ) and phthalic anhydride. Contrary to prior indications 1 can be hydrolyzed in the presence of acid at temperatures greater than 200 giving excellent yields of 2.

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