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

HRID 439606Notes

Reaction equation

HRID 439606 reaction equation
ClCl.[C:3]([Cl:7])(Cl)(Cl)Cl.[CH:8]([C:11]1[NH:12][C:13]([CH2:18][OH:19])=C(CO)[N:15]=1)([CH3:10])[CH3:9]>C(O)C>[CH:8]([C:11]1[NH:12][C:13]([CH2:18][OH:19])=[C:3]([Cl:7])[N:15]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 136089212-Isopropyl-4,5-bis(hydroxymethyl) imidazoleHCID 86737392Chlorine tetrachloromethane

Product 1

HCID 15338147[4-chloro-2-(1-methylethyl)-1H-imidazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customa temperature of 40° C.
  2. additionAfter the dropwise addition
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionAfter the residual brown oil was dissolved in water
  5. additionsodium carbonate was added
  6. customThe mixture was evaporated again under reduced pressure
  7. customThe obtained resulting solid product
  8. extractionwas extracted with ethanol
  9. customthe extract was evaporated under reduced pressure
  10. extractionthe resulting solid product was extracted with cold water
  11. custom0.71 Grams of the starting 2-isopropyl-4,5-bis(hydroxymethyl) imidazole was recovered as the extraction residue
  12. extractionthe extract
  13. customafter evaporate under reduced pressure

Sources & evidence

ORD record
ord-87f5783324074cec91b1ed9b74aa5e35
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

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