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

HRID 602845Notes

Reaction equation

HRID 602845 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][CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+].O>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][CH:20]=[CH:19]2)=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8027PyrroleHCID 11430Potassium CarbonateHCID 120399992,5-dichloro-4'-fluorobenzophenon

Product 1

HCID 59165206(2,5-Dichlorophenyl)[4-(1H-pyrrol-1-yl)phenyl]methanoneYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °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 134.6 g (0.500 mol) of 2,5-dichloro-4′-fluorobenzophenone, 50.3 g (0.750 mol) of pyrrole, 76.0 g (0.550 mol) of potassium carbonate and 840 ml of dehydrated N,N′-dimethylacetamide. The reaction solution was heated under a nitrogen atmosphere in an oil bath at 100° C. for 3 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 2.5 L of toluene. The solution was washed with salt solution using a separating funnel 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 133.3 g was obtained. The crude product was subjected to recrystallization using a hexane/ethyl acetate mixed solvent, and the resultant crystal was isolated. As a result, 125.3 g (0.396 mol) of an objective purified product was obtained with a yield of 79.3%.

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 solution was washed with salt solution
  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. customthe resultant crystal was isolated

Sources & evidence

ORD record
ord-00098d2514614c1d9c5b57d63572a894
Source dataset
uspto-grants-2011_03
Patent number
US07906608B2

Reaction notes

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