Ethanol → (5-Chloro-2-ethyl-1h-imidazol-4-yl)methanol
Reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[NH:12][C:13]([CH2:18][OH:19])=[C:14](CO)[N:15]=1)[CH3:10].C(O)C>O1CCOCC1>[CH2:9]([C:11]1[NH:12][C:13]([CH2:18][OH:19])=[C:14]([Cl:1])[N:15]=1)[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.76 Grams (13.2 mmol) of the N-chlorosuccinimide was added little by little to a solution consisting of 2.06 g (13.2 mmol) of an ethyl-4,5-bis(hydroxymethyl) imidazole, 100 ml of ethanol and 40 ml of 1,4-dioxane maintained at room temperature with stirring over a period of about 11 minutes. The mixture was then stirred at the same temperature for three hours and for another 30 minutes at a temperature of 50° C. After the reaction, the solvent was distilled off under reduced pressure and the resulting yellowish oily product was subjected to the column chromatography (silica gel-acetone), and the obtained effluent was evaporated to dryness under reduced pressure. By using acetonitrile, the resulting solid product was recrystallized three times to obtain a colorless crystalline 2-ethyl-4-chloro-5-(hydroxymethyl) imidazole in an amount of 0.82 g (yield, 39.0%). The TLC and spectra of this compound were the same as the properties exhibited by the above-mentioned 2-ethyl-4-chloro-5-(hydroxymethyl) imidazole.
Workup
- stirringThe mixture was then stirred at the same temperature for three hours and for another 30 minutes at a temperature of 50° C
- customAfter the reaction
- distillationthe solvent was distilled off under reduced pressure
- customthe obtained effluent was evaporated to dryness under reduced pressure
- customthe resulting solid product was recrystallized three times
Sources & evidence
- ORD record
- ord-9189c98df87a41c28f678d26cd8e4adb
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05514811
Reaction notes
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