N-Alkylation And Hydrolysis Of Benzamide And Its Derivatives

N-alkylation of amide (benzamide, salicylamide, phthalamic acid) and a-branched primary alcohol (tertiary butanol and1-benzyl ethanol) was performed in this work. The Bronsted (PWA) was used as catalysts at the advantages of cheap and easy recovery. The influences of solvents, temperature, alcohol/amide ratio, and reaction time effect on the reaction were investigated. The optimal conditions is HCOOH,80oC,4.0,12h. Under the optimal conditions, yield of N-tertiary butyl salicylamide is50%and yield of N-(1-Phenyl) ethyl salicylamide is68%. The corresponding yield of N-alkylation of benzamide is42%and56%. And then, The influences of adjacent group (-H,-OH,-OAc,-H2,-NHAc,-COOH) on the reaction were investigated. The results show that N-alkylation reaction was facilitated when adjacent group was-OH and-OAc. Furthermore, acidity and alkaline hydrolysis of N-alkylation amide was studied. The results show that the hydrolysis yield of N-tertiary butyl phthalamic acid, N-tertiary butyl salicylamide, N-tertiary butyl benzamide under the optimal conditions ([H]=3mol/L,100oC,10h) is81%,53%,41%. And, the hydrolysis yield of N-tertiary butyl phthalamic acid, N-tertiary butyl salicylamide, N-tertiary butyl benzamide under the optimal conditions ([OH]=3mol/L,100"C,10h) is90%,38%,56%.