Acyl iodides in organic synthesis. Reactions of acetyl iodide with urea, thiourea, and their N,N′-disubstituted derivatives

Acetyl iodide reacted with urea and its derivatives to give the corresponding N-substituted products. The reactions of acetyl iodide with thiourea, N,N ′-dimethylthiourea, imidazolidine-2-thione, and hexahydropyrimidine-2-thione resulted in the formation of S - or N -acetyl derivatives, depending on...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2009-04, Vol.45 (4), p.486-490
Main Authors: Voronkov, M. G., Vlasova, N. N., Grigor’eva, O. Yu, Belousova, L. I., Vlasov, A. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Acetyl iodide reacted with urea and its derivatives to give the corresponding N-substituted products. The reactions of acetyl iodide with thiourea, N,N ′-dimethylthiourea, imidazolidine-2-thione, and hexahydropyrimidine-2-thione resulted in the formation of S - or N -acetyl derivatives, depending on the temperature and structure of the sulfur functionality (thione or thiol). By contrast, in the reaction of acetyl iodide with N,N ′-bis(3-triethoxysilylpropyl)thiourea one ethoxy group on the silicon atom was replaced by iodine with formation of N -{3-[(diethoxy)iodosilyl]propyl}- N ′-[3-(triethoxysilyl)propyl]thiourea. The latter decomposed on heating to give 3-triethoxysilylpropyl isothiocyanate and silicon-containing polymer with the composition C 45 H 97 IN 6 O 14.5 S 3 Si 6 .
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428009040022