N,N-Dimethylaniline → 99951-44-7

HRID 973830Notes

Reaction equation

HRID 973830 reaction equation
O[C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=[C:6]2[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=[C:6]2[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178499043HCID 178499043, compound

Product 1

HCID 1676769199951-44-7Yield 91.3%

Procedure

To a suspension of the product obtained in Step 1 (50 g) in 700 ml of phosphorus oxychloride 31 g of N,N-dimethylaniline was dropwise added at room temperature over a period of 20 minutes. The mixture was refluxed for one hour, excess phosphorus oxychloride was removed by distillation under normal pressure, and the reddish brown residue was dissolved in 2 liters of chloroform. This solution was slowly poured into 1.5 liters of ice-cooled saturated sodium bicarbonate solution, the chloroform layer was collected after shaking, and the aqueous layer was again extracted with fresh chloroform. The organic layers were joined together, washed with 800 ml of saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The dried solution was concentrated under reduced pressure to about 100 ml, and 200 ml n-hexane was added to this concentrate, giving 47 g of the objective compound as colorless crystals.

Workup

  1. additionwas dropwise added at room temperature over a period of 20 minutes
  2. temperatureThe mixture was refluxed for one hour
  3. customexcess phosphorus oxychloride was removed by distillation under normal pressure
  4. dissolutionthe reddish brown residue was dissolved in 2 liters of chloroform
  5. additionThis solution was slowly poured into 1.5 liters of ice-
  6. temperaturecooled saturated sodium bicarbonate solution
  7. customthe chloroform layer was collected
  8. extractionthe aqueous layer was again extracted with fresh chloroform
  9. washwashed with 800 ml of saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationThe dried solution was concentrated under reduced pressure to about 100 ml, and 200 ml n-hexane
  12. additionwas added to this concentrate

Sources & evidence

ORD record
ord-4b0472f71b8b4ac3ae20534609e94c8c
Source dataset
uspto-grants-1991_11
Patent number
US05064953

Reaction notes

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