Acrylonitrile → 4-(Dimethylamino)benzonitrile

HRID 1789084Notes

Reaction equation

HRID 1789084 reaction equation
C(#N)C=C.[CH3:5][N:6]([CH3:16])[C:7]1[CH:15]=[CH:14][C:10]([CH:11]=[N:12]O)=[CH:9][CH:8]=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:5][N:6]([CH3:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 351532HCID 351532, compound

Product 1

HCID 709674-(Dimethylamino)benzonitrileYield 90.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 7237O-XyleneSolvent2×

Conditions

Temperature
135 °C

Procedure

A solution of 53 g of acrylonitrile and 1.0 g of copper(II) acetate in 100 g of o-xylene was heated to the boil (85° C.), after which a solution of 82 g of p-dimethylaminobenzaldoxime in 110 g of o-xylene was added dropwise by heating further. During the addition, the boiling point of the reaction mixture increased to 135° C. The mixture was stirred under reflux for a further 30 minutes and was then left to cool. The precipitated acrylamide was filtered off under suction, and the mother liquor was extracted by shaking with a little water. The organic phase was evaporated down and the residue was taken up in 400 ml of petroleum ether. After the mixture had been left to stand overnight at 0° C., 66 g (90%) of p-dimethylaminobenzonitrile were obtained in the form of yellow crystals of melting point 75°-76° C.

Workup

  1. temperatureby heating further
  2. additionDuring the addition
  3. temperatureunder reflux for a further 30 minutes
  4. waitwas then left
  5. temperatureto cool
  6. filtrationThe precipitated acrylamide was filtered off under suction
  7. extractionthe mother liquor was extracted
  8. stirringby shaking with a little water
  9. customThe organic phase was evaporated down
  10. waitAfter the mixture had been left

Sources & evidence

ORD record
ord-c71aa7c41c254ef8940038a9e76a0288
Source dataset
uspto-grants-1987_08
Patent number
US04686302

Reaction notes

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