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

HRID 562450
Notes
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Reaction equation

HRID 562450 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
  • concentrationthe reaction mixture is concentrated under reduced pressure
  • customThe residue is triturated with diethyl ether
  • filtrationfiltered off
  • washwashed with diethyl ether
  • Sources & evidence

    ORD record
    ord-00e041146182450b850d5077fcfcfa55
    Source dataset
    uspto-grants-2011_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08067407B2

    Reaction notes

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