Benzoylacetonitrile → 2-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrile

HRID 1355696Notes

Reaction equation

HRID 1355696 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[C:1]([C:9](=[CH:14][N:15]([CH3:17])[CH3:16])[C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 64799BenzoylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrileYield 100.2%

Procedure

Following the method of Toche et al. (Org. Prep. Proc. Intl. 1998, 39, 367), a mixture of 5.0 g (34.4 mmol) benzoylacetonitrile and 9.2 ml (69.0 mmol) N,N-dimethylformamide dimethyl acetal was stirred for 1 hour at room temperature. The reaction mixture was then concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was dried with sodium sulfate. Concentration in vacuo afforded 6.9 g (100%) 2-benzoyl-3-dimethylaminoacrylonitrile as a yellow oil which was used in the next step without further purification. ES-MS m/e (%):223 (M+Na+, 40), 201 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2cece331e73c4335b951d09a8ba2bc0c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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