Pyridine → 1,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole

HRID 584725

Reaktionsgleichung

Reaktionsgleichung von HRID 584725
[F:1][C:2]([F:16])([F:15])[C:3](=[N:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[NH2:4].N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=O)=[CH:27][CH:26]=1>O1CCOCC1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:29]([C:28]3[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)=[N:4][C:3]([C:2]([F:15])([F:16])[F:1])=[N:5]2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 696776222,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

Produkt 1

HCID 102914551,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazoleAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (0.92 g, 3.95 mmol) in 10 mL of dioxane, were added pyridine (0.319 mL, 3.95 mmol) and a solution of 4-methoxybenzoyl chloride (673 mg, 3.95 mmol) in 3 mL of dioxane. The mixture was refluxed with stirring for 12 hours. The solvent was removed under reduced pressure. 50 mL of dichloromethane and 20 mL of 0.1 N hydrochloric acid were added to the residue and the organic layer was separated. The aqueous layer was extracted with 50 mL of dichloromethane. A combined organic layer was washed with 0.1 N hydrochloric acid and brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (toluene-ethyl acetate 9:1) and then recrystallized with diisopropyl ether-hexane to give pale brown needle of 1,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (0.67 g, 48.6% yield).

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. customThe solvent was removed under reduced pressure
  3. addition50 mL of dichloromethane and 20 mL of 0.1 N hydrochloric acid were added to the residue
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with 50 mL of dichloromethane
  6. washA combined organic layer was washed with 0.1 N hydrochloric acid and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (toluene-ethyl acetate 9:1)
  10. customrecrystallized with diisopropyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-8c802859d6794e89b1ed4ca9ec73cd50
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927230B2

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