Phenylacetonitrile → 18226-50-1

HRID 440965Notes

Reaction equation

HRID 440965 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CO>[C:8]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:12][N:13]([CH3:15])[CH3:14])#[N:9]

Participants

4

Reactant 2

HCID 8794PhenylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 379784318226-50-1Yield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 5.1 grams (0.044 mole) of benzyl cyanide and 8.7 grams (0.065 mole) of N,N-dimethylformamide dimethyl acetal in 150 mL of methanol was heated at reflux for about 20 hours. After this time gas chromatographic analysis of the reaction mixture indicated that the reaction was not complete. An additional 3.0 mL of the intermediate acetal (total--0.088 mole) was added, and the heating at reflux was continued an additional 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was triturated with 25% methylene chloride in petroleum ether, yielding 5.9 grams of 1-cyano-1-phenyl-2-(N,N-dimethylamino)ethene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 20 hours
  2. temperaturethe heating at reflux
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  4. customThe residue was triturated with 25% methylene chloride in petroleum ether

Sources & evidence

ORD record
ord-d610a429205e461a93a26da816f5a56d
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

Loading…