Designing of thermally stable amide functionalized benzimidazolium perchlorate ionic liquid for transamidation of primary carboxamides
•Designed Amide functionalized benzimidazolium perchlorate ionic liquid catalyst.•A metal and solvent free catalytic system for the transamidation is established.•Catalyst based on perchlorate anion exhibited maximum catalytic activity.•Transamidation of aromatic and aliphatic amides with variety of amines carried out.•Catalyst shown very good thermal stabilitiy and recyclability.
In the present work, we have designed and synthesized a thermally stable catalyst based on functionalized benzimidazolium perchlorate ionic liquid and tested its efficacy towards metal free and solvent free transamidation of amides and amines. The ionic liquid comprising the perchlorate ion has shown remarkably better activity than those which contain other anions and accordingly a plausible mechanism for the catalytic activity is arrived. The developed catalytic system has shown excellent activity towards the transamidation of alicyclic and aromatic amines with acetamide, benzamide and p-nitrobenzamide under mild conditions. Furthermore, the transamidation of nicotinamide with benzylamine in presence of the ionic liquid catalyst was found to occur with very good yields and thus provides a facile route for the synthesis of pharmaceutically significant compounds. The catalyst has exhibited very good thermal stability upto 203 °C and very good recyclability upto 5 runs without significant loss in its activity.
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Journal: Applied Catalysis A: General - Volume 493, 5 March 2015, Pages 158–167