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
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.