N,N-Dimethylaniline → HCID 19989194, compound

HRID 973832Notes

Reaction equation

HRID 973832 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]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][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]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178499049HCID 178499049, compound

Product 1

HCID 19989194HCID 19989194, compound

Procedure

To a suspension of the product obtained in Step 1 (35 g) in 400 ml phosphorus oxychloride, 24 g of N,N-dimethylaniline 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 reddish brown oil left was dissolved in 1.5 liters of chloroform. This solution was slowly poured into 800 ml of ice-cooled saturated sodium bicarbonate solution, the chloroform layer was collected after thorough mixing, and the aqueous layer was again extracted with one liter of fresh chloroform. The organic layers were joined together, washed with 500 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 of n-hexane was added to this concentrate, giving 20 g of the objective compound as faint yellow 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 reddish brown oil left
  5. dissolutionwas dissolved in 1.5 liters of chloroform
  6. additionThis solution was slowly poured into 800 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 one liter of fresh chloroform
  10. washwashed with 500 ml of saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationThe dried solution was concentrated under reduced pressure to about 100 ml, and 200 ml of n-hexane
  13. additionwas added to this concentrate

Sources & evidence

ORD record
ord-44f3bbd52785449dbc1789f5be530194
Source dataset
uspto-grants-1991_11
Patent number
US05064953

Reaction notes

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