The Formation of 2,2,4-Trimethyl-2,3-dihydro-1H-1,5-Benzodiazepine from 1,2-Diaminobenzene in the Presence of Acetone

Autor: Felix Odame, Phumelele Kleyi, Eric Hosten, Richard Betz, Kevin Lobb, Zenixole Tshentu
Jazyk: angličtina
Rok vydání: 2013
Předmět:
Zdroj: Molecules, Vol 18, Iss 11, Pp 14293-14305 (2013)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules181114293
Popis: In an attempt to synthesize a 2-substituted benzimidazole from the reaction of o-phenylenediamine and isophthalic acid in the presence of acetone and ethanol under microwave irradiation, a salt of the isophthalate ion and 2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepin-5-ium ion was obtained. The condensation of two moles of acetone with the amine groups resulted in the formation of the benzodiazepine which crystallized as an iminium cation forming a salt with the isophthalate anion. The formation of benzodiazepine was also confirmed by performing the reaction of o-phenylenediamine with excess acetone in ethanol under conventional heating conditions. The compounds were characterized by NMR, FTIR, HRMS and microanalysis as well as X-ray crystallography. The reaction mechanism leading to the formation of benzodiazepine is also discussed.
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