Alkylation of 3,5-Dimethylpyrrole-2,4-Dicarboxylic Acid 2-Ethyl 4-Methyl Diester and Its Relatives
Webster, David M.
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In order to improve the herbicidal activity of 3,5-dimethylpyrrole dicarboxylic acid 2-ethyl-4-methyl ester, a slow acting but effective herbicide, the pyrrole was N-acylated or alkylated. In reactions of the sodium salt of the pyrrole with acid chlorides containing an a-hydrogen, the N-acyl product was formed as expected. A second major product was also produced, one in which the oxygen of the Nacyl group of the mono acyl product had bonded to the carbonyl carbon of a second molecule of acid chloride. The extent of formation of this second order product was studied using different orders of addition, solvents, and several pyrroles.