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

HRID 1717336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717336
[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[OH:15])=[N+:2]=[N-:3].[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[C:17]#[CH:18]>C1(C)C=CC=CC=1>[CH2:11]([NH:10][C:8]([C:7]1[CH:13]=[CH:14][C:4]([N:1]2[CH:18]=[C:17]([C:16]([O:20][CH2:21][CH3:22])=[O:19])[N:3]=[N:2]2)=[C:5]([OH:15])[CH:6]=1)=[O:9])[CH3:12]

Komponenten

4

Edukt 2

HCID 12182Ethyl propiolateHCID 866298074-azido-N-ethyl-3-hydroxybenzamide

Produkt 1

HCID 68517012ethyl 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxylateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-azido-N-ethyl-3-hydroxybenzamide (2.71 g) obtained in Example 133b) in toluene (65 ml) was added ethyl propiolate (2.0 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 washed with dichloromethane to give the title compound as a brown solid (2.70 g, 68%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight under a nitrogen atmosphere
  3. customthe solvent was evaporated under reduced pressure
  4. washThe residue was washed with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-98c21802083643ceb7f9059f9928f1e7
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803822B2

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