Next Article in Journal
Synthesis of Quaternary Heterocyclic Salts
Previous Article in Journal
Triterpenoids and Steroids from Ganoderma mastoporum and Their Inhibitory Effects on Superoxide Anion Generation and Elastase Release
Article Menu

Export Article

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

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

Department of Chemistry, Nelson Mandela Metropolitan University, P.O. Box 77000, Port Elizabeth 6031, South Africa
Department of Chemistry, Rhodes University, P.O. Box 94, Grahamstown 6140, South Africa
Author to whom correspondence should be addressed.
Received: 11 September 2013 / Revised: 11 November 2013 / Accepted: 11 November 2013 / Published: 19 November 2013
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [376 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: o-phenylenediamine; acetone; benzodiazepine o-phenylenediamine; acetone; benzodiazepine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top