N,N-Dimethylaniline → HCID 19989193, compound

HRID 973834Notes

Reaction equation

HRID 973834 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](O)[N:5]2[N:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=[C:4]2[N:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:6]1[N:5]2[N:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=[C:4]2[N:3]=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178499045HCID 178499045, compound

Product 1

HCID 19989193HCID 19989193, compound

Procedure

To a suspension of the product obtained in Step 1 (50 g) in 500 ml of phosphorus oxychloride, N,N-dimethylaniline (30 g) was dropwise added at room temperature, the mixture was refluxed for two hours, excess phosphorus oxychloride was removed by distillation under normal pressure, and the black oil left was dissolved in 200 ml of chloroform. This solution was slowly poured into 200 ml of ice-cooled saturated sodium bicarbonate solution, the chloroform layer was collected after thorough mixing, and the aqueous layer was again extracted with 200 ml of fresh chloroform. The combined organic layers were washed with 100 ml of saturated sodium chloride solution and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure to about 50 ml, and 100 ml of n-hexane was added to this concentrate, giving 49 g of the objective compound as colorless crystals.

Workup

  1. additionwas dropwise added at room temperature
  2. temperaturethe mixture was refluxed for two hours
  3. customexcess phosphorus oxychloride was removed by distillation under normal pressure
  4. waitthe black oil left
  5. dissolutionwas dissolved in 200 ml of chloroform
  6. additionThis solution was slowly poured into 200 ml of ice-
  7. temperaturecooled saturated sodium bicarbonate solution
  8. customthe chloroform layer was collected after thorough mixing
  9. extractionthe aqueous layer was again extracted with 200 ml of fresh chloroform
  10. washThe combined organic layers were washed with 100 ml of saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationThe dried solution was concentrated under reduced pressure to about 50 ml, and 100 ml of n-hexane
  13. additionwas added to this concentrate

Sources & evidence

ORD record
ord-c9d10345b9204bd3a4d37389511c2c85
Source dataset
uspto-grants-1991_11
Patent number
US05064953

Reaction notes

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