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

HRID 1442460Notes

Reaction equation

HRID 1442460 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]methanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

134.6 g (0.500 mol) of 2,5-dichloro-4′-fluorobenzophenon, 50.3 g (0.750 mol) of pyrrole, 76.0 g (0.550 mol) of potassium carbonate, and 840 ml of N,N′-dimethylacetamide were added into a 2 L three-necked flask equipped with a stirrer, thermometer, cooling pipe, and nitrogen inlet tube. The reaction solution was heated by use of an oil bath and was allowed to react at 100 degrees C. in a nitrogen atmosphere for 3 hours. After the disappearance of material was confirmed by a thin layer chromatography, the mixture was cooled to ambient temperature. Then, the reaction solution was gradually poured into 3 L of water to cause coagulation. The product obtained by filtration was dissolved into 2.5 L of toluene was added, and then, by using a separating funnel washed by brine until the water layer becomes neutral. After the organic layer was dried by magnesium sulfate, the solvent was removed by an evaporator. The rough yield was 133.3 g. By using mixture solvent of hexane and ethyl acetate, the dried product was recrystallized for isolation to obtain 125.3 g (0.396 mol) of the intended refining material in 79.3% in yield.

Workup

  1. customequipped with a stirrer
  2. temperaturethermometer, cooling pipe, and nitrogen inlet tube
  3. temperatureThe reaction solution was heated by use of an oil bath
  4. customto react at 100 degrees C
  5. customThe product obtained by filtration
  6. additionwas added
  7. washwashed by brine until the water layer
  8. dry with materialAfter the organic layer was dried by magnesium sulfate
  9. customthe solvent was removed by an evaporator
  10. customthe dried product was recrystallized for isolation
  11. customto obtain 125.3 g (0.396 mol) of the intended refining material in 79.3%
  12. customin yield

Sources & evidence

ORD record
ord-eff5b04108484748a4d746c6ef990c44
Source dataset
uspto-grants-2010_02
Patent number
US07658867B2

Reaction notes

Loading…