Journal of the American Chemical Society

Ortho Esters, Imidic Esters and Amidines. VII. N-Alkylformanilides from Alkyl Orthoformates and Primary Aromatic Amines; Rearrangement of Alkyl N-Arylformimidates1

RM Roberts, PJ Vogt

Index: Roberts; Vogt Journal of the American Chemical Society, 1956 , vol. 78, p. 4778,4780

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Citation Number: 43

Abstract

The major ptoduct of the reaction of an alkyl orthoformate and a primary aromatic amine in the presence of sulfuric acid catalyst at temperatures above 140" has been shown to be an N-alkylformanilide. Alkyl N-arylformimidates, which are the major products of these same reactants at lower temperatures, undergo molecular rearrangement to N-alkylformanilides at higher temperatures under the influence of sulfuric acid, Good yields of several S- ...