Ethyl propiolate → ethyl 1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylate

HRID 1717331Notes

Reaction equation

HRID 1717331 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[O:15][CH2:16][CH3:17])=[N+:2]=[N-:3].[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[C:19]#[CH:20]>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:5]1[CH:6]=[C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])[CH:13]=[CH:14][C:4]=1[N:1]1[CH:20]=[C:19]([C:18]([O:22][CH2:23][CH3:24])=[O:21])[N:3]=[N:2]1)[CH3:17]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 866298054-azido-3-ethoxy-N-ethylbenzamide

Product 1

HCID 68516073ethyl 1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-azido-3-ethoxy-N-ethylbenzamide (0.70 g) obtained in Example 131d) in toluene (30 ml) was added ethyl propiolate (0.61 ml), and the mixture was heated under reflux overnight under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) to give the title compound as a white powder (0.59 g, 60%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight under a nitrogen atmosphere
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-32afa223d9b54fb7b73083a770d3d9ed
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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