Dimethylformamide → 3-(Dimethylamino)-2-acetylacrylonitrile

HRID 2199561Notes

Reaction equation

HRID 2199561 reaction equation
[O:1]=[C:2]([CH3:6])[CH2:3][C:4]#[N:5].CC(N(C)C)=O.[CH3:13][N:14]([CH:16]=O)[CH3:15]>>[CH3:15][N:14](/[CH:16]=[C:3](/[C:2](=[O:1])[CH3:6])\[C:4]#[N:5])[CH3:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 31374DimethylacetamideHCID 755793-Oxobutyronitrile

Product 1

HCID 299417973-(Dimethylamino)-2-acetylacrylonitrile

Procedure

3-Oxo-butyronitrile (113 g, 1.36 mol) and DMF.DMA (215 g, 1.81 mol) were heated to 80° C. for two hours. The solvents were then removed under vacuum to yield a solid. The solid was partitioned between ethyl acetate (1.5 L) and saturated sodium bicarbonate solution (1 L). The layers were separated and the aqueous layer was extracted with ethyl acetate (1.5 L). The organic layers were combined and the solvent removed under vacuum to yield the title compound as a solid.

Workup

  1. customThe solvents were then removed under vacuum
  2. customto yield a solid
  3. customThe solid was partitioned between ethyl acetate (1.5 L) and saturated sodium bicarbonate solution (1 L)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (1.5 L)
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-f16af318563e476ab93b9ceca2b13c1e
Source dataset
uspto-grants-2016_06
Patent number
US09359327B2

Reaction notes

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