Dimethylformamide diethylacetal → Ethyl 3-(N,N-dimethylamino)-2-(4-cyano-1H-imidazol-1-yl)acrylate

HRID 562448Notes

Reaction equation

HRID 562448 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1)#[N:2].C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>>[CH3:17][N:18]([CH:20]=[C:8]([N:6]1[CH:7]=[C:3]([C:1]#[N:2])[N:4]=[CH:5]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:19]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 68753735ethyl 2-(4-cyano-1H-imidazol-1-yl)acetate

Product 1

HCID 66726020Ethyl 3-(N,N-dimethylamino)-2-(4-cyano-1H-imidazol-1-yl)acrylate

Procedure

3.8 g (21.4 mmol) of the compound from Example 1A and 7.4 ml (6.3 g, 42.8 mmol) of N,N-dimethylformamide diethyl acetal are stirred at a bath temperature of 100° C. for 16 h. For work-up, the cooled reaction solution is concentrated on a rotary evaporator and the residue is dried under reduced pressure. Yield: 5.0 g (73% pure, 73% of theory)

Workup

  1. customFor work-up, the cooled reaction solution
  2. concentrationis concentrated on a rotary evaporator
  3. customthe residue is dried under reduced pressure

Sources & evidence

ORD record
ord-69bf8ffb63744d2681bddc2f56be05ca
Source dataset
uspto-grants-2011_11
Patent number
US08067407B2

Reaction notes

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