"The iodide salts of the 1,3-alkylated imidazoles are readily prepared by quaternization of the nucleophilic nitrogen of N-substituted imidazoles with alkyl iodides. ... Direct alkylation by the appropriate chloroalkanes proved to be more successful. In some cases the product was obtained in high yield and was quite pure, even without recrystallation. The procedure for reactions using chloromethane or chloroethane (both gases) consisted of heating the homogeneous mixture of 1-alkylimidazole and chloroalkane in a sealed vessel. Excess chloroalkane was removed by evaporation and the residue was almost pure product. NMR analysis of the residue showed nearly 100% conversion. In the case of liquid chloroalkanes, reactions were run by refluxing mixtures of the reactants, using excess chloroalkane as solvent. The formation of VIII was relatively slow under these conditions, but was much more rapid when run in a sealed tube at 80 C. Proton NMR provides a convenient way to monitor the extent of reaction for all of the imidazolium salts, since there is no overlap of reactant and product resonances. In those compounds the C-2 proton resonance in the salt is shifted considerably downfield from the position in the neutral 1-methylimidazole, and it is exchangeable with D2O."--Results and discussion, p. 4-5.

Title from cover. "January 1981." "Air Force Systems Command, United States Air Force."--Cover. "Project 2303."--Cover. "This document was prepared by the Electrochemistry Division, Directorate of Chemical Sciences, Frank J. Seiler Research Laboratory, United States Air Force Academy, CO. The research was conducted under Project Work Unit Number 2303-F2-10, Organic and Inorganic Electrochemical Measurements. Dr. John S. Wilkes was the Project Scientist in charge of the work."--Cover verso. "This report describes the preparation of a series of heterocyclic chlorides that were used as the basis of some ambient temperature chloro-aluminate molten salts. Details for the syntheses and the NMR and IR spectra are not normally published in journals, therefore they are documented here to establish a complete record of this phase of our research in chloro-aluminate molten salts."--Preface. Also available as ADA094772.