On-Column Gas Chromatographic Synthesis of 1,3-Dialkyl (C = 1.10), Benzyl, and Cyclohexyl Barbiturate Derivatives

Abstract

Procedures are described for the on-column gas chromatographic synthesis of various N-alkyl-N-alkyl barbiturates where groups added to the nitrogens are benzyl, cyclohexyl, or straight chains with 1 to 10 carbons. The 1,3-dialkyl barbiturates having methyl, ethyl, n-propyl, n-butyl, cyclohexyl, isopropyl, or t-butyl groups can be prepared on-column by injecting an aliquot of a chloroform solution of the barbiturate with the appropriate N,N-dimethylfor-mamide dialkyl acetal. The 1,3-dialkyl barbiturates where benzyl or butyl through decyl groups are added can be similarly prepared with N,N-dimethylformamide dineopentyl acetal and the appropriate alcohol to yield the desired compound. The 1-alkyl(I)-3-alkyl-(II) barbiturates where the alkyl groups differ are prepared by on-column reaction of a barbiturate with aliquots of each of the respective reagents giving the desired groups.