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

HRID 1749419Notes

Reaction equation

HRID 1749419 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[C:2]([C:3](=[CH:14][N:15]([CH3:17])[CH3:16])[C:4]#[N:5])(=[O:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 64799BenzoylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrileYield 8%

Procedure

A solution of 3-oxo-3-phenylpropanenitrile (1.0 equiv.) in 1,1-dimethoxy-N,N-dimethylmethanamine (2.2 M) was stirred at 50° C. under nitrogen overnight. After reaction completion, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (30% ethyl acetate in petroleum ether) to afford 2-benzoyl-3-(dimethylamino)acrylonitrile (8% yield) as a yellow oil. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 7.83 (s, 1H), 7.61-7.60 (m, 2H), 7.52-7.50 (m, 1H), 7.47-7.45 (m, 2H), 3.37 (s, 3H), 3.28 (s, 3H); MS (ESI) m/z=201.2 [M+1]+.

Workup

  1. customAfter reaction completion
  2. concentrationthe reaction mixture was concentrated
  3. customThe residue was purified by silica gel column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-eebe88f55e7e4dfdb6469a3dd01caa60
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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