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Molecules 2013, 18(11), 14293-14305; doi:10.3390/molecules181114293
Communication

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

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Received: 11 September 2013; in revised form: 11 November 2013 / Accepted: 11 November 2013 / Published: 19 November 2013
(This article belongs to the Section Organic Synthesis)
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Abstract: 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.
Keywords: o-phenylenediamine; acetone; benzodiazepine o-phenylenediamine; acetone; benzodiazepine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Odame, F.; Kleyi, P.; Hosten, E.; Betz, R.; Lobb, K.; Tshentu, Z. The Formation of 2,2,4-Trimethyl-2,3-dihydro-1H-1,5-Benzodiazepine from 1,2-Diaminobenzene in the Presence of Acetone. Molecules 2013, 18, 14293-14305.

AMA Style

Odame F, Kleyi P, Hosten E, Betz R, Lobb K, Tshentu Z. The Formation of 2,2,4-Trimethyl-2,3-dihydro-1H-1,5-Benzodiazepine from 1,2-Diaminobenzene in the Presence of Acetone. Molecules. 2013; 18(11):14293-14305.

Chicago/Turabian Style

Odame, Felix; Kleyi, Phumelele; Hosten, Eric; Betz, Richard; Lobb, Kevin; Tshentu, Zenixole. 2013. "The Formation of 2,2,4-Trimethyl-2,3-dihydro-1H-1,5-Benzodiazepine from 1,2-Diaminobenzene in the Presence of Acetone." Molecules 18, no. 11: 14293-14305.


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