Phosphorus oxychloride → N,N-dimethyl-N'-(2-cyano-4,5-dimethoxyphenyl)acetamidine

HRID 542212Notes

Reaction equation

HRID 542212 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]([N:9]([CH3:11])[CH3:10])=O.[C:12]([C:14]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:15]=1[NH2:16])#[N:13]>C(Cl)(Cl)Cl>[CH3:10][N:9]([CH3:11])[C:7](=[N:16][C:15]1[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:14]=1[C:12]#[N:13])[CH3:6]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 7359672-Amino-4,5-dimethoxybenzonitrile

Product 1

HCID 13359979N,N-dimethyl-N'-(2-cyano-4,5-dimethoxyphenyl)acetamidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Phosphorous oxychloride (1.0 ml) was added to a stirred solution of dimethylacetamide (2.8 ml) in chloroform (10 ml) at room temperature. The mixture was stirred for 5 minutes, 2-cyano-4,5-dimethoxyaniline (1.78 g) added and the reaction stirred under reflux for 4 hours. The mixture was cooled, poured onto ice and extracted with chloroform and the organic phase discarded. The aqueous layer was basified (solid NaOH) extracted with chloroform, the combined extracts washed with water, dried (Na2SO4) and evaporated in vacuo. A sample of the brown oily residue (2 g) was crystallised from diisopropylether to give N,N-dimethyl-N'-(2-cyano-4,5-dimethoxyphenyl)acetamidine, m.p. 94°-96°.

Workup

  1. stirringthe reaction stirred
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. additionpoured onto ice
  5. extractionextracted with chloroform
  6. extractionextracted with chloroform
  7. washthe combined extracts washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customA sample of the brown oily residue (2 g) was crystallised from diisopropylether

Sources & evidence

ORD record
ord-6861312998fd4b0ab960bed51ede74b6
Source dataset
uspto-grants-1987_04
Patent number
US04656174

Reaction notes

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