Реакция #78657

Уравнение реакции

dioxane

4-hydroxymethyl-2-methoxymethyl-1-methylimidazole

5-hydroxymethyl-2-methoxymethyl-1-methylimidazole

N-chlorosuccinimide

→

title compound

5-Chloro-4-hydroxymethyl-2-methoxymethyl-1-methylimidazole

Растворители

ethylene glycol monoethylether

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONThen the solvent was distilled off in vacuo
2. 2
   Другоеthe crude product purified by chromatography (silica gel; methylene chloride/ethanol=99:1 to 90:10)

Методика

A 1:1 mixture of 7.7 g (49 mmol) of 4-hydroxymethyl-2-methoxymethyl-1-methylimidazole and 5-hydroxymethyl-2-methoxymethyl-1-methylimidazole and 7.3 g (55 mmol) of N-chlorosuccinimide was heated to 50° C. in 48 mL of ethylene glycol monoethylether and 70 mL of dioxane for 10 hours. Then the solvent was distilled off in vacuo and the crude product purified by chromatography (silica gel; methylene chloride/ethanol=99:1 to 90:10) to obtain the isomerically pure title compound. Yield: 3.4 g (36% of theory); Rf value: 0.40 (silica gel; methylene chloride/ethanol=19:1).

Источник