Imidazole → (2,5-Dichlorophenyl)[4-(1H-imidazol-1-yl)phenyl]methanone

HRID 2389226Notes

Reaction equation

HRID 2389226 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](F)=[CH:8][CH:7]=1)=[O:5].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 120399992,5-dichloro-4'-fluorobenzophenon

Product 1

HCID 59165210(2,5-Dichlorophenyl)[4-(1H-imidazol-1-yl)phenyl]methanoneYield 87.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

150.7 g (0.560 mol) of 2,5-dichloro-4′-fluorobenzophenone, 114.4 g (1.68 mol) of imidazole, 100.6 g (0.728 mol) of potassium carbonate, and 840 mL of N,N-dimethyl acetamide were weighed in a 2 L three-necked flask equipped with a stirrer, thermometer, cooling pipe, and nitrogen inlet tube. The reaction solution was heated to 110° C. using an oil bath for 2 hours under a nitrogen atmosphere. After confirming the disappearance of raw materials by way of thin-layer chromatography, the reaction liquid was allowed to cool to room temperature. Thereafter, the reaction liquid was gradually added to 3 L of water, the product was solidified and filtered. The product obtained by filtering was dissolved in THF (1.2 L), toluene (4 L) was added, and the mixture was washed with a sodium chloride solution till the aqueous layer became neutral. The organic layer was dried using magnesium sulfate, and then the solvent was removed by an evaporator. The approximate yield amount was 180 g. The crude product was subjected to a recrystallization separating operation using a mixed solvent of 1 L toluene and 20 mL methanol heated at 80° C. to obtain 155 g of a white solid at a yield of 87%.

Workup

  1. customequipped with a stirrer
  2. temperaturethermometer, cooling pipe, and nitrogen inlet tube
  3. customfor 2 hours
  4. customthe reaction liquid
  5. temperatureto cool to room temperature
  6. customThereafter, the reaction liquid
  7. filtrationfiltered
  8. customThe product obtained
  9. filtrationby filtering
  10. dissolutionwas dissolved in THF (1.2 L)
  11. additiontoluene (4 L) was added
  12. washthe mixture was washed with a sodium chloride solution till the aqueous layer
  13. customThe organic layer was dried
  14. customthe solvent was removed by an evaporator
  15. customThe crude product was subjected to a recrystallization
  16. customseparating operation
  17. temperatureheated at 80° C.

Sources & evidence

ORD record
ord-9d6842b13dbb4a04a153f0f3b969c5cf
Source dataset
uspto-grants-2012_09
Patent number
US08273499B2

Reaction notes

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