By Gould R.F. (ed.)

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It doea not, however, establish the tautomeric character of the imidasoles, as a difference in stability of the two isomers might also favor the formation of only one compound. The virtually tautomeric character of 4 (or 5 )-methylimidaaole follows from its behavior on methylation, leading to the formation of a mixture, separable by distillation, of 1,&dimethyl- and 1,4dimethylimidazole (66,67). Thus the compound reacts as if it were a mixture of 4-methyl- and 5-methylimidseole. l-DimcthylimidnzoIc Iiiiidazoles containing a, free iiiiino lrytlrogcn arc thus virtually bausystem and react like tautoriieric iiiixtures of the two possible Corms.

The compound melts at 275O, distils without decomposition, and exhibits great chemical stability, especially under acid conditions. The addition of metals or metal aniides to its solution in liquid ammonia results in the formation of salts (70). These hydrolyze when dissolved in water with the formation of lophinc and a metal hydroxide. Exposure 11. Alkyl- and Arylimidazoles . 47 to hydrogen iodide at 300" brings about a slow conversion of lophine into benzoic acid (71); treatment with sodium in alcohol leaves the compound unchanged (53).

O=x-j NHs 3/ \ N Lophine tended it t o the preparation of simpler imidazoles and demonstrated its general applicability. It occurred to him that the formation of imidazole from glyoxal and ammonia, as discovered by Debus (3), might proceed in a manner similar t o the lophine synthesis, imidazole formation being due to tlie interaction of (tiiiiuonia, glyoxal, and foriiialdehydc. The formaldehyde, he reasoned, might arise from the cleavage of the glyoxal 33 34 Chemistry of Classes and Derivatives under the influence of ammonia.

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