Imidazole → 1-Dodecylimidazole

Participants

Reaction Steps

A stirred mixture of 9.96 g. of dodecyl bromide (40 mM), 5.44 g. of imidazole (80 mM), 100 ml. of 0.97N NaOH (97 mM), 100 ml. of PhH, and 336 mg. of Aliquat 336 (1 mM; methyltricaprylylammonium chloride) was refluxed for 23 h. The benzene layer was separated, washed with brine containing a little NaOH, and evaporated. The residue was purified of a little front-running and some origin impurities by quick chromatography on 150 g. of silica gel with 1:1 CH2Cl2 --EtOAc (Rf 0.35), affording 7.48 g. of single-spot material which was distilled at ca. 0.5 Torr (bp 144° C.) to give 6.97 g. of pure product (74%): NMR 7.5 (s, 1H), 7.1 (br s, 1H), 6.95 (br s, 1H), 3.95 (t, J=7 Hz, 2H), 1.85 (m, 2H), 1.3 (s, 18H), 1.0 ppm (m, 3H).

Provenance & Evidence