N,N-Dimethylaniline → HCID 13562765, compound

HRID 973826Notes

Reaction equation

HRID 973826 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[N:10]([N:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=2)[C:11]=1O)=[O:5])[CH3:2].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:31])=O>>[Cl:31][C:11]1[N:10]2[N:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:9]2[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178469692HCID 178469692, compound

Product 1

HCID 13562765HCID 13562765, compound

Procedure

The product obtained in Step 1 (12 g) was suspended in 100 ml of phosphorus oxychloride, 5.9 g of N,N-dimethylaniline was added dropwise to this suspension at 0° C. with stirring over a period of ten minutes, and the mixture was stirred at room temperature for 30 minutes and then refluxed for four hours. Removing excess phosphorus oxychloride by distillation under normal pressure gave about 50 ml of a reddish brown oil. It was dissolved in 300 ml of dichloromethane, the solution was washed with 500 ml of saturated sodium bicarbonate solution, then with 80 ml of saturated sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The dried reddish yellow filtrate was concentrated to about 30 ml, and crystallized from 20 ml of n-hexane, affording 8.5 g of the objective compound as faint yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. temperaturerefluxed for four hours
  3. distillationRemoving excess phosphorus oxychloride by distillation under normal pressure

Sources & evidence

ORD record
ord-4197be3aca7d4028ba2dd46d65c8239c
Source dataset
uspto-grants-1991_11
Patent number
US05064953

Reaction notes

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