Potassium Carbonate → HCID 3715801, compound

HRID 274577Notes

Reaction equation

HRID 274577 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[C:19](=O)([O-])[O-:20].[K+].[K+]>CN(C=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 20092951HCID 20092951, compound

Product 1

HCID 3715801HCID 3715801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To ice-cooled DMF (4.0 g) was added phosphorous oxychloride (8.4 g) dropwise and the mixture was stirred at room temperature for 15 minutes. To the stirred reaction mixture was added a solution of 1-(2-chloro-4-methylphenyl)pyrrole (9.7 g) in DMF (8 ml) dropwise and the mixture was stirred at 50° C. for 1.5 hours followed by addition of ice-water. Stirring was continued for a while and then the mixture was made basic with potassium carbonate, and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-hexane afforded yellow prisms (7.1 g, 59%), m.p. 111°-112° C.

Workup

  1. customTo the stirred reaction mixture
  2. stirringthe mixture was stirred at 50° C. for 1.5 hours
  3. stirringStirring
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel
  9. customto give crystals
  10. customRecrystallization from ethyl acetate-hexane afforded yellow prisms (7.1 g, 59%), m.p. 111°-112° C.

Sources & evidence

ORD record
ord-b7aded1f56ba489695316f944428d229
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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