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Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™

Author:
Bousfield, Thomas W., Pearce, Katharine P. R., Nyamini, Simbarashe B., Angelis-Dimakis, Athanasios, Camp, Jason E.
Source:
Green chemistry 2019 v.21 no.13 pp. 3675-3681
ISSN:
1463-9270
Subject:
boiling, chlorides, dimethylformamide, green chemistry, heat production, methylene chloride, primary amines, solvents, standard operating procedures, toxicity, wastes
Abstract:
Cyrene™ as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene™ is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene™ resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene™ found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.
Agid:
6489124