Dimethylformamide → HCID 57780058, compound

HRID 2427083Notes

Reaction equation

HRID 2427083 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[OH-].[Na+].CN(C)[CH:23]=[O:24]>>[Cl:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[C:8]=1[N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:23]=[O:24]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 207882021-(2,6-Dichlorophenyl)-1H-pyrrole

Product 1

HCID 57780058HCID 57780058, compoundYield 33.7%

Procedure

Under ice-cooling, 7.67 g of phosphorus oxychloride was added dropwise to 4 g of N,N-dimethylformamide. The mixture was stirred at room temperature for 30 minutes, and 2.1 g of 1-(2,6-dichlorophenyl)-1H-pyrrole was added thereto. The resulting mixture was stirred at 60° C. for 2 hours, allowed to cool to room temperature, and then poured into ice water. The mixture was adjusted to pH 4 by an addition of a 2N aqueous sodium hydroxide solution, and then extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.80 g of 1-(2,6-dichlorophenyl)-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. temperatureUnder ice-cooling
  2. stirringThe resulting mixture was stirred at 60° C. for 2 hours
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate two times
  5. washwashed successively with water
  6. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d31d576c2eba49c79187b9dc6c64f286
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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