Imidazole → 25700-00-9

HRID 1735743Notes

Reaction equation

HRID 1735743 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C(=O)([O-])[O-].[K+].[K+]>[Cu]=O.N1C=CC=CC=1>[N:11]1([C:2]2[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 165023'-Bromoacetophenone

Product 1

HCID 1428797925700-00-9Yield 15.4%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 25 g of 3'-bromoacetophenone, 9.0 g of imidazole, 18 g of anhydrous potassium carbonate, 1.0 g of copper oxide (CuO) and 30 ml of pyridine is refluxed for 64 hours. The mixture is cooled to room temperature, filtered and the filter cake washed with 50 ml of pyridine and 3×50 ml of dichloromethane. The combined filtrates are concentrated to dryness under vacuum. The residue is partitioned between 250 ml of dichloromethane and 150 ml of water. The emulsion is clarified by filtration through a pad of diatomaceous earth. The organic layer is separated, dried (MgSO4) and filtered through a pad of hydrous magnesium silicate. The pad is washed with 50 ml of dichloromethane and the combined filtrate is concentrated on a steam bath to 150 ml and while hot 300 ml of hexane is added. The mixture is cooled to room temperature, activated carbon added and the mixture filtered through diatomaceous earth. The filtrate is cooled to -10° C. and filtered to give 3.6 g of crystals, mp 69°-71° C. The filtrate is treated with activated carbon, filtered and the filtrate evaporated to give 12 g of crystals, mp 62°-65° C.

Workup

  1. temperatureis refluxed for 64 hours
  2. filtrationfiltered
  3. washthe filter cake washed with 50 ml of pyridine and 3×50 ml of dichloromethane
  4. concentrationThe combined filtrates are concentrated to dryness under vacuum
  5. customThe residue is partitioned between 250 ml of dichloromethane and 150 ml of water
  6. filtrationThe emulsion is clarified by filtration through a pad of diatomaceous earth
  7. customThe organic layer is separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered through a pad of hydrous magnesium silicate
  10. washThe pad is washed with 50 ml of dichloromethane
  11. concentrationthe combined filtrate is concentrated on a steam bath to 150 ml and while hot 300 ml of hexane
  12. additionis added
  13. temperatureThe mixture is cooled to room temperature
  14. additionactivated carbon added
  15. filtrationthe mixture filtered through diatomaceous earth
  16. temperatureThe filtrate is cooled to -10° C.
  17. filtrationfiltered

Sources & evidence

ORD record
ord-e8dda607d09247e8bb5cc281827d6960
Source dataset
uspto-grants-1996_07
Patent number
US05538977

Reaction notes

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