Mechanosynthesis of N-Methyl Imines Using Recyclable Imidazole-Based Acid-Scavenger: In Situ Formed Ionic Liquid as Catalyst and Dehydrating Agent

Khaligh, Nader Ghaffari and Ong, Chiu Ling and Mihankhah, Taraneh and Johan, Mohd Rafie and Juan, Joon Ching (2019) Mechanosynthesis of N-Methyl Imines Using Recyclable Imidazole-Based Acid-Scavenger: In Situ Formed Ionic Liquid as Catalyst and Dehydrating Agent. Australian Journal of Chemistry, 72 (3). pp. 194-199. ISSN 0004-9425, DOI https://doi.org/10.1071/CH18408.

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Official URL: https://doi.org/10.1071/CH18408

Abstract

1,1′-(1,4-Butanediyl)bis(imidazole) was prepared by a modified method and its application as an efficient promoter was demonstrated for the mechanosynthesis of N-methyl imines using ball milling as a non-conventional process under solvent-free conditions. In this new protocol design, the bis-imidazole acted as a recyclable acid-scavenging agent. This efficient approach to the N-methyl imines displays a combination of the synthetic virtues of a non-conventional condensation reaction with ecological benefits and convenience of a facile mechanosynthetic process. The current method has advantages such as reduced waste by avoiding solvent, exclusion of hazardous materials during the reaction, elimination of handling an anhydrous gas in an evacuated container or a solution of methylamine in ethanol, good yields for relatively unreactive benzaldehydes containing electron-donating substituents, short reaction times, and metal- and acid-free conditions. Furthermore, the promoter was easily regenerated and reused several times with no significant loss of activity. © 2019 CSIRO.

Item Type: Article
Funders: University of Malaya for the partial financial support
Uncontrolled Keywords: Ball milling; Condensation reactions; Dehydration; Ionic liquids; Materials handling
Subjects: Q Science > QD Chemistry
T Technology > TA Engineering (General). Civil engineering (General)
Divisions: Deputy Vice Chancellor (Research & Innovation) Office > Nanotechnology & Catalysis Research Centre
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 23 Apr 2020 14:38
Last Modified: 23 Apr 2020 14:38
URI: http://eprints.um.edu.my/id/eprint/24230

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