Iranian Journal of Chemistry

Iranian Journal of Chemistry

1,3-Disulfonic acid imidazolium chloride as a highly efficient catalyst for the synthesis of N,N′-alkylidene bisamides

Document Type : Original Article

Authors
Soheila Kaman-Torki 1
Abdolkarim Zare 2
1 Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
2 Department of Chemistry, Payame Noor University, P.O Box: 19395-3697 Tehran, Iran
10.22036/ijc.2019.163561.1052
Abstract
In this research, a highly efficient new method for the synthesis of N,N′-alkylidene bisamides has been introduced. The reaction between aromatic aldehydes and primary amides in the presence of acidic ionic liquid 1,3-disulfonic acid imidazolium chloride ([Dsim]Cl) under solvent-free conditions afforded these compound in high yields and in short times.
Amide functional group is of importance in chemical and medicinal industries. For example, bisamides have been extensively applied in the synthesis of peptide- and pseudo-peptide-containing biological materials, and other medicinal compounds. The best method for the preparation of N,N′-alkylidene bisamide is the condensation reaction between amide and aldehyde; several catalysts have been reported for this reaction.
However, the previous methods for the synthesis of these amide derivatives have drawbacks, as following: high reaction temperature, moderate yields, long reaction times, difficult procedure for catalyst preparation, the use of toxic and volatile organic solvents as reaction media, and no agreement with green chemistry protocols. Thus, introducing new catalysts for this reaction, which have not these drawbacks, is of importance.

Graphical Abstract

1,3-Disulfonic acid imidazolium chloride as a highly efficient catalyst for the synthesis of N,N′-alkylidene bisamides
Keywords
Alkylidene bisamide
Acidic ionic liquid
Disulfonic acid imidazolium chloride ([Dsim]Cl)
Solvent-free reaction
Primary amide
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Iranian Journal of Chemistry
Volume 2, Issue 2 - Serial Number 3
February 2020
Pages 119-125

  • Receive Date 20 December 2018
  • Revise Date 11 February 2019
  • Accept Date 24 February 2019