2-Isopropyl-4,5-bis(hydroxymethyl) imidazole → [4-chloro-2-(1-methylethyl)-1H-imidazol-5-yl]methanol

Participants

Reaction Steps

26.3 Grams (15.6 mmol) of a 4.2% chlorine-carbon tetrachloride solution was dropwisely added to a solution consisting of 2.52 g (14.8 mmol) of the 2-isopropyl-4,5-bis(hydroxymethyl) imidazole and 200 ml of ethanol maintaining a temperature of 40° C. with stirring. After the dropwise addition has been finished, the stirring was continued at 40° C. for one hour and, then, the solvent was distilled off under reduced pressure. After the residual brown oil was dissolved in water, sodium carbonate was added thereto to make the mixture alkaline. The mixture was evaporated again under reduced pressure. The obtained resulting solid product was extracted with ethanol, the extract was evaporated under reduced pressure, and the resulting solid product was extracted with cold water. 0.71 Grams of the starting 2-isopropyl-4,5-bis(hydroxymethyl) imidazole was recovered as the extraction residue, and the extract after evaporate under reduced pressure was subjected to the column chromatography (silica gel-acetone) to obtain a 2-isopropyl-4-chloro-5-(hydroxymethyl) imidazole in an amount of 0.56 g (yield, 30.3% with respect to the starting material consumed). By using acetonitrile, the compound was further refined. The TLC and spectra of this compound were measured to be the same as those of Example 4.

Provenance & Evidence