100907-80-0Relevant articles and documents
Carbodiimides as important intermediates in the reaction of isocyanates with carboxylic acids
Schotman, A. H. M.,Mijs, W. J.
, p. 88 - 91 (1992)
The reaction between isocyanates and carboxylic acids is known to lead to amides.We have studied the mechanism of catalysis of this reaction by phospholene oxides. The reaction between phenyl isocyanates and benzoic acid was monitored under various conditions using High-Pressure Liquid Chromatography.It was found that the catalyst reacts with the isocyanate under formation of a carbodiimide.The carbodiimide reacts with the carboxylic acid to form amide and isocyanate via an N-acylurea as intermediate.The catalyst is partly deactivated by the acid.The phospholene catalyst was only found effective in reactions with aromatic isocyanates.
Oxidative desulfurization of disubstituted thioureas using Pb(II) salts and investigation of pKa-dependent regioselective N-acylation
Ghosh, Harisadhan,Sarkar, Soumya,Ali, Abdur Rezzak,Patel, Bhisma K.
experimental part, p. 1 - 11 (2010/10/01)
A highly efficient method for the N-acylation of both symmetrical and unsymmetrical thioureas by the use of lead (II) salts and triethylamine has been achieved. The reaction gives regioselective N-acylated product for unsymmetrical thiourea. For unsymmetrical thiuourea, regioselective N-acylation takes place towards the amine having lower pKa.A linear correlation between the pKas of the amines and the regioselective Nacylation is found. Another attractive feature of this transformation is that lead sulfide, which is important to material science, is obtained as a side product (nanocubes of 20 nm).
Mechanism of the reaction of carbodiimides with carboxylic acids
Schotman, A. H. M.
, p. 319 - 324 (2007/10/02)
The kinetic parameters of the reaction of diphenylcarbodiimide with various carboxylic acids have been determined at a temperature interval of 20-160 deg C.The classical scheme for the reaction of carbodiimides with carboxylic acids is extended.It has been found that, at high temperatures, amides and isocyanates are the end products of the reactions.N-Acylureas, initially formed from aromatic carbodiimides and carboxylic acids, dissociate into isocyanates and amides at temperatures above 60 deg C.N-Acylureas formed by the reaction of carboxylic acids with aliphatic carbodiimides prove to be more stable: their dissociation temperature is about 50 deg C higher.Both the formation and dissociation of N-acylureas are much faster when the parent acid is stronger.