4,5-DIMETHYLIMIDAZOLE - A CORRECTION AND ALTERNATIVE SYNTHESIS

被引：16

作者：

DSA, A

COHEN, LA

机构：

[1] Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 07期

关键词：

D O I：

10.1002/jhet.5570280730

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fractional vacuum distillation of the product obtained from thermal condensation of acetoin with formamide is a formic acid complex of 4,5-dimethylimidazole, and not the expected free base. The H-1 and C-13 nmr spectra suggest that the product may be closer to a 1:1 hydrogen-bonded adduct than to a true salt. Commercial 4-hydroxymethyl-5-methylimidazole is converted quantitatively to the 4-chloromethyl derivative with thionyl chloride; hydrogenolysis of the latter compound provides 4,5-dimethylimidazole in an overall 80-90% yield, doubling the yield obtained by the classical method.

引用

页码：1819 / 1820

页数：2

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