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Reactions of fatty acid chlorides: II. Synthesis of monohydrazides or dihydrazides by acylation of hydrazine hydrate with saturated fatty acid chlorides
Author(s) -
Sonntag Norman O. V.
Publication year - 1968
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02667173
Subject(s) - hydrazine (antidepressant) , acylation , chemistry , hydrate , stearic acid , chloride , myristic acid , fatty acid , organic chemistry , acetyl chloride , palmitic acid , catalysis , chromatography
The acylation of hydrazine hydrate with a series of saturated fatty acid chlorides containing from eight to 18 carbon atoms was studied under a variety of conditions in order to obtain the desirable fatty acid monohydrazides. Optimum yields were obtained (ranging from 31.5% to 75% as the series ascended from C‐8 to C‐18) for the even‐numbered monohydrazide members through the use of a large excess of hydrazine hydrate in several organic solvents. Diethyl ether was found to be suitable if the acid chloride is dissolved in it and added slowly to a cold mixture of hydrazine hydrate in ether. The Schotten‐Baumann technique was found suitable for the preparation of the symmetrically substituted fatty acid dihydrazides in better than 82% yields when one mole of hydrazine hydrate was acylated with two of acid chlorides. Physical and chemical properties of both series of fatty nitrogen derivatives are briefly treated. Stearic monohydrazide was condensed with acetonylacetone to give a substituted pyrrole. An unsymmetrical dihydrazide was prepared by the acylation of myristic monohydrazide with lauroyl chloride. Stearic dimethylhydrazide was prepared by the acylation of dimethylhydrazine with stearoyl chloride. Two quaternizations of this product were carried out.