Ethyl Acetate → 2-n-Butyl-5-hydroxymethyl-4-iodoimidazole

Participants

Reaction Conditions

Reaction Steps

4-DMAP (1.2 g; 10 mmol) and N-iodosuccinimide (25 g; 111 mmol) were added to a solution of 2-butyl-4-hydroxymethyl-imidazole (15.4 g; 100 mmol) in dioxane (210 ml) and 2-methoxyethanol (140 ml) and the mixture was stirred overnight at 50° C. Concentration gave 44.4 g of a brownish-yellow magma (theory; 28 g), which was further reacted without further purification. For characterisation, 2 g of the crude product were dissolved using ethyl acetate and washed with 5% NaHCO3 solution and saturated sodium chloride solution. Drying and concentration of the organic phases gave 1.2 g of a yellow solid [97% of theory; m.p.: 135°-40° C. (dec.); Rf : 0.24 (methylene chloride:methanol=10:1)].

Provenance & Evidence