3-Oxobutyronitrile → 3-(Dimethylamino)-2-acetylacrylonitrile

HRID 1876756Notes

Reaction equation

HRID 1876756 reaction equation
[O:1]=[C:2]([CH3:6])[CH2:3][C:4]#[N:5].[CH3:7][N:8]([CH:10](OC)OC)[CH3:9]>>[CH3:9][N:8](/[CH:10]=[C:3](/[C:2](=[O:1])[CH3:6])\[C:4]#[N:5])[CH3:7]

Participants

3

Reactant 2

HCID 755793-OxobutyronitrileHCID 78373Dimethylformamide dimethyl acetal

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-6c8b7030cc8946009711943d809dd598
Source dataset
uspto-grants-2012_11
Patent number
US08309720B2

Reaction notes

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