Imidazole → 1-Crotylimidazole

Participants

Reaction Steps

Crotyl chloride (3.2 g; 35 m mole) in methanol (35 ml) was added dropwise with stirring during 3.5 hours to a refluxing mixture of imidazole (11.9 g; 175 m mole) and sodium bicarbonate (2.95 g; 35 m mole) in methanol (35 ml). When the addition was complete the reaction mixture was refluxed for 24 hours, the solvent evaporated and the residue dissolved in water (60 ml) and extracted with chloroform (3×20 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (25 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residue was fractionally distilled to yield 1-crotylimidazole as a colourless oil, b.p. 123°-124° C./18 mmHg.

Provenance & Evidence