Acrylonitrile → 3-(3,5-Dimethylanilino)propanenitrile

HRID 1107971Notes

Reaction equation

HRID 1107971 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[C:10](#[N:13])[CH:11]=[CH2:12].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH3:8])[CH:5]=1)[NH:1][CH2:12][CH2:11][C:10]#[N:13]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 79493,5-DimethylanilineHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate

Product 1

HCID 2926323-(3,5-Dimethylanilino)propanenitrileYield 62.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

3,5-Xylidine (5.0 g) and acrylonitrile (2.3 g) were dissolved in acetic acid (2 ml), and the mixture was stirred at 60° C. for 20 hr. Ethyl acetate (200 ml) was added to the reaction mixture and neutralized with saturated aqueous solution of sodium hydrogencarbonate. The mixture was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzene=1/10-1/3) to give 4.5 g of oily β-(3,5-dimethylanilino)propionitrile.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzene=1/10-1/3)

Sources & evidence

ORD record
ord-271b81b6c3414b6990f914a350a6fff3
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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