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

HRID 2039473Notes

Reaction equation

HRID 2039473 reaction equation
C(O[CH:4](OCC)[N:5]([CH3:7])[CH3:6])C.[N:11]1([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=[CH:14][N:13]=[N:12]1>>[CH3:4][N:5]([CH3:7])[CH:6]=[C:16]([N:11]1[CH:15]=[CH:14][N:13]=[N:12]1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 10103365ETHYL 2-(1H-1,2,3-TRIAZOL-1-YL)ACETATE

Product 1

HCID 66726233Ethyl 3-(dimethylamino)-2-(1H-1,2,3-triazol-1-yl)acrylate

Conditions

Temperature
100 °C

Procedure

44.2 ml (38.0 g, 257.8 mmol) of N,N-dimethylformamide diethyl acetal are added to 20.0 g (128.9 mmol) of the compound from Example 2A, and the mixture is stirred at 100° C. for 16 h. After cooling to RT, the reaction mixture is concentrated under reduced pressure. The residue is triturated with diethyl ether, filtered off and washed with diethyl ether. Yield: 18.0 g (67% of theory)

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customThe residue is triturated with diethyl ether
  4. filtrationfiltered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-87d3b6d3bb9945b698f5e3b3104785bd
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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