Dimethylformamide → 3-(Dimethylamino)-2-acetylacrylonitrile

HRID 1523321Notes

Reaction equation

HRID 1523321 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-7b2d4c0a756f4d59b1e0fb96fe9c150c
Source dataset
uspto-grants-2015_07
Patent number
US09079882B2

Reaction notes

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