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

HRID 2039470Notes

Reaction equation

HRID 2039470 reaction equation
[N:1]1([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=[CH:4][N:3]=[CH:2]1.C(O[CH:15](OCC)[N:16]([CH3:18])[CH3:17])C>>[CH3:15][N:16]([CH:18]=[C:6]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:17]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 3798501ethyl 2-(1H-imidazol-1-yl)acetate

Product 1

HCID 66726242Ethyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylate

Procedure

38.0 g (244.9 mmol) of the compound from Example 3A are stirred in 126 ml (108.1 g, 734.7 mmol) of N,N-dimethylformamide diethyl acetal at a bath temperature of 90° C. for 16 h. After cooling, the mixture is concentrated under reduced pressure, the residue is stirred with diisopropyl ether and the solid is filtered off and finally washed with diisopropyl ether. Yield: 49.0 g (95% of theory)

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated under reduced pressure
  3. filtrationthe solid is filtered off
  4. washfinally washed with diisopropyl ether

Sources & evidence

ORD record
ord-98bb628635084af8b27d295441a165e0
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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