Benzoylacetonitrile → 2-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrile
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]=1Participants
3
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
- concentrationThe reaction mixture was then concentrated in vacuo