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

HRID 602844Notes

Reaction equation

HRID 602844 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+].O>C1COCC1.C1(C)C=CC=CC=1>[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

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 120399992,5-dichloro-4'-fluorobenzophenon

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A 2-L three-necked flask equipped with a stirrer, a thermometer, a condenser tube and a nitrogen inlet tube was charged with 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′-dimethylacetamide. The reaction solution was heated under a nitrogen atmosphere in an oil bath at 110° C. for 2 hours. After thin layer chromatography confirmed that the materials showed no peaks, the reaction liquid was allowed to cool to room temperature. The reaction liquid was slowly added to 3 L of water, and the product was precipitated. The liquid was then filtered. The product obtained by the filtration was dissolved in THF (1.2 L), and toluene (4 L) was added to the solution. The mixture was washed with salt solution until the water phase became neutral. The organic phase was dried over magnesium sulfate, and the solvent was evaporated with an evaporator. A crude product weighing 180 g was obtained. The crude product was subjected to recrystallization using 1 L of toluene and 20 ml of methanol in combination at 80° C., and the resultant crystal was isolated. As a result, 155 g of a white solid was obtained with a yield of 87%. A 1H-NMR spectrum of the compound is shown in FIG. 1.

Workup

  1. customA 2-L three-necked flask equipped with a stirrer
  2. customthe reaction liquid
  3. temperatureto cool to room temperature
  4. customThe reaction liquid
  5. customthe product was precipitated
  6. filtrationThe liquid was then filtered
  7. customThe product obtained by the filtration
  8. washThe mixture was washed with salt solution until the water phase
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. customthe solvent was evaporated with an evaporator
  11. customwas obtained
  12. customThe crude product was subjected to recrystallization
  13. customat 80° C.
  14. customthe resultant crystal was isolated

Sources & evidence

ORD record
ord-5912d04d2f424eb19274c916ad60ce25
Source dataset
uspto-grants-2011_03
Patent number
US07906608B2

Reaction notes

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