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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.