The Journal of Organic Chemistry

Alkylation of N, N-Dimethylamides via Carbanion Intermediates

HL Needles, RE Whitfield

Index: Needles,H.L.; Whitfield,R.E. Journal of Organic Chemistry, 1966 , vol. 31, p. 989 - 990

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Citation Number: 13

Abstract

A dialkylated amide, 2-butyl-N, N-dimethylhexan-amide, was isolated only in the reaction of N, N-dimethylacetamide with n-butyl bromide. When excess sodium amide was used in this alkylation (see Table I), the yield of 2-butyl-N, N-dimethylhexanamide increased, and traces of other side products were detected by glpc. Reaction of N, N-dimethylacetamide was not complete even when 2 moles of sodium amide/mole of amide w: zs used. We believe ...