Dimethylformamide dimethyl acetal → Ethyl 3-(dimethylamino)-2-isocyanoacrylate
Reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>C(O)C>[CH2:7]([O:6][C:4](=[O:5])[C:3]([N+:1]#[C-:2])=[CH:11][N:12]([CH3:14])[CH3:13])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl isocyanoacetate (5.0 g) in ethanol (100 mL) is added N,N-dimethyl-formamide dimethyl acetal (6.5 g) dropwise with stirring over 10 minutes. The reaction is stirred for 24 hours and the ethanol is evaporated. The resulting oil is passed through magnesium silicate using 50% ethyl acetate-hexanes as the eluant. The solvents are removed and the resulting oil is crystallized from ethyl acetate-hexanes to yield light yellow needles, 3.0 g.
Workup
- stirringThe reaction is stirred for 24 hours
- customthe ethanol is evaporated
- customThe solvents are removed
- customthe resulting oil is crystallized from ethyl acetate-hexanes
- customto yield light yellow needles, 3.0 g
Sources & evidence
- ORD record
- ord-1d5aaa5544c04479b148f344ae0c9798
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380243B1
Reaction notes
Loading…