Dimethylformamide → 3-(Dimethylamino)-2-acetylacrylonitrile
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
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
- customThe solvents were then removed under vacuum
- customto yield a solid
- customThe solid was partitioned between ethyl acetate (1.5 L) and saturated sodium bicarbonate solution (1 L)
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (1.5 L)
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-e9583e48cd5d43308f8bba3f3344d405
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006432B2
Reaction notes
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