Ethanol → (5-Chloro-2-ethyl-1h-imidazol-4-yl)methanol

Reaction equation

[Cl:1]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[CH2:13]([C:15]1[NH:16][C:17]([CH2:22][OH:23])=[C:18](CO)[N:19]=1)[CH3:14].C(O)C>O1CCOCC1>[CH2:13]([C:15]1[NH:16][C:17]([CH2:22][OH:23])=[C:18]([Cl:1])[N:19]=1)[CH3:14]

Participants

Procedure

1.53 Grams (6.6 mmol) of trichloroisocyanuric acid was added little by little to a solution consisting of 2.03 g (13 mmol) of the 2-ethyl-4,5-bis(hydroxymethyl) imidazole, 100 ml of ethanol and 40 ml of 1,4-dioxane at room temperature with stirring over a period of about 10 minutes. The mixture was stirred at the same temperature for one hour, the solvent was distilled off under reduced pressure, the reaction product was extracted with ethanol, and the extract was evaporated to dryness under reduced pressure. The resulting solid product was then extracted with acetone, the extract was concentrated and was then subjected to the column chromatography (silica gel-acetone), and the effluent was further concentrated and was recrystallized from acetonitrile to obtain a 2-ethyl-4-chloro-5-(hydroxymethyl) imidazole in an amount of 0.78 g (yield, 37.4%). The TLC and spectra were measured to be the same as those of Example 3.