1978
DOI: 10.1002/jhet.5570150410
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Synthesis of 1,3‐dihydro‐2H‐benzimidazol‐2‐one from 2‐aminobenzamide

Abstract: 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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Cited by 7 publications
(4 citation statements)
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“…We prepared a series of benzimidazolones by the reaction of the appropriate derivative of o -phenylenediamine with 1,1‘-carbonyldiimidazole (Scheme ). Compound 1-H 2 has been previously synthesized by several alternative routes. The best solvents for crystallizing 1-H 2 , 1-(CH 3 ) 2 , 1-Cl 2 , 1-Br 2 , 1-I 2 , and 2-H 2 were polar protic and aprotic solvents: hot methanol, warm dimethylformamide, pyridine, and N - methylpyrolidinone. The initial dissolution of the compounds usually required a large amount of hot solvent (1−3 L/g of solute).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…We prepared a series of benzimidazolones by the reaction of the appropriate derivative of o -phenylenediamine with 1,1‘-carbonyldiimidazole (Scheme ). Compound 1-H 2 has been previously synthesized by several alternative routes. The best solvents for crystallizing 1-H 2 , 1-(CH 3 ) 2 , 1-Cl 2 , 1-Br 2 , 1-I 2 , and 2-H 2 were polar protic and aprotic solvents: hot methanol, warm dimethylformamide, pyridine, and N - methylpyrolidinone. The initial dissolution of the compounds usually required a large amount of hot solvent (1−3 L/g of solute).…”
Section: Resultsmentioning
confidence: 99%
“…Compound 1-H 2 has been previously synthesized by several alternative routes. [28][29][30][31][32] The best solvents for crystallizing 1-H 2 , 1-(CH 3 ) 2 , 1-Cl 2 , 1-Br 2 , 1-I 2 , and 2-H 2 were polar protic and aprotic solvents: hot methanol, warm dimethylformamide, pyridine, and N-meth- -Fc 2 |/∑Fo 2 for all σ. d Calculated using the program Cerius2. 34 e Solvent used for the growth of single crystals for X-ray crystallograhy.…”
Section: Resultsmentioning
confidence: 99%
“…HRMS analyses were carried out using a Bruker‐micro‐TOF‐Q‐MS analyzer (Bruker Corporation: Karlsruhe, DE). The 2‐aminobenzamides were prepared from isatoic anhydride and amines according to reference .…”
Section: Methodsmentioning
confidence: 99%
“…1 H -Benzo[ d ]imidazol-2(3 H )-one 7 is very readily available by the reaction of urea with o -phenylenediamine. , Compound 7 has been reported to be stable toward acid or base hydrolysis under normal conditions . The alkylation of 7 has been described in a number of papers. The reaction of 7 with unactivated aromatic bromide (e.g., 4-bromoanisole) with a CuI catalyst in toluene at reflux for 24 h gave an 82% yield of the diaryl-substituted product .…”
mentioning
confidence: 99%