DIRECT SYNTHESIS OF AMIDES FROM CARBOXYLIC-ACIDS AND AMINES WITH PHENYLDICHLOROPHOSPHITE AS REAGENT IN AQUEOUS-MEDIUM

Citation
Ci. Chiriac et al., DIRECT SYNTHESIS OF AMIDES FROM CARBOXYLIC-ACIDS AND AMINES WITH PHENYLDICHLOROPHOSPHITE AS REAGENT IN AQUEOUS-MEDIUM, Revue Roumaine de Chimie, 38(11), 1993, pp. 1327-1331
Citations number
9
Categorie Soggetti
Chemistry
Journal title
ISSN journal
00353930
Volume
38
Issue
11
Year of publication
1993
Pages
1327 - 1331
Database
ISI
SICI code
0035-3930(1993)38:11<1327:DSOAFC>2.0.ZU;2-Q
Abstract
Amides with aliphatic and aromatic structure have been prepared by a d irect condensation reaction between carboxylic acids and amines in aqu eous medium, using phenyldichlorophosphite as reagent. The realisation of this reaction in the presence of water is a prove that diacylpheny lphosphites, which result in situ as intermediary products (leaving gr oups), have a relative stability to hydrolysis and react with amines, affording amides in moderate yields (31-54%). This reaction has a biol ogical importance, because the realisation of amide bond in biological syntheses of proteines, polypeptides etc. occurs also in aqueous medi um. The yields of this reaction increase at 30-40-degrees and decrease at 90-100-degrees, because in this last case the hydrolytic reactions become preponderent in comparison with the condensation reactions.