Abstract
N, N'-Alkylidenebisacetamide, such as N, N'-methylenebisacetamide, N, N'-ethylidenebisacetamide, and N, N'-benzylidenebisacetamide, reacted smoothly with 2, 4-xylenol by the interaction of phosphoryl chloride, affording N-(α-alkyl-2-hydroxy-3, 5-dimethylbenzyl) acetamide by substitution of α-acetamidoalkyl group, in a good yield. Effect of the amide residues in N, N'-alkylidenebisamide on the reaction was examined with N, N'-methylenebisformamide, -acetamide, -propionamide, and -benzamide. The general reaction sequence was presumed and found to be characterized by the formation of a nitrile as a by-product corresponding to the one amide residue in N, N'-alkylidenebisamide.
