Phosphorus oxychloride → HCID 19759297, compound

HRID 248363Notes

Reaction equation

HRID 248363 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.[C:19](=O)(O)[O-:20].[Na+]>CN(C)C=O>[Cl:6][C:7]1[N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]([CH:19]=[O:20])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 19759392HCID 19759392, compound

Product 1

HCID 19759297HCID 19759297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

Phosphoryl chloride (747 μl) was added dropwise to N,N-dimethylformamide (7 ml) at 5° C. The mixture was stirred at 5° C. for 15 minutes and at ambient temperature for 15 minutes. To the mixture was added a solution of 2-chloro-1-(4-methylphenyl)pyrrole (1.2 g) in N,N-dimethylformamide (7 ml) at ambient temperature. The mixture was stirred at the same temperature for one hour and at 50° C. for 2.5 hours. After cooled to ambient temperature, the mixture was treated with saturated aqueous sodium bicarbonate solution. The separated oil was extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated in vacuo. The residue was column chromatographed on silica gel to yield 5-chloro-1-(4-methylphenyl)pyrrole-2-carbaldehyde (377 mg) as a solid.

Workup

  1. stirringThe mixture was stirred at the same temperature for one hour and at 50° C. for 2.5 hours
  2. temperatureAfter cooled to ambient temperature
  3. extractionThe separated oil was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-3412258ae1a04a7ebe5f95c2a93b5e00
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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