2-Fluoroaniline → 3-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole

HRID 6935

Reaktionsgleichung

Reaktionsgleichung von HRID 6935
[CH2:1]([O:8][CH2:9][C:10]([NH:12][NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[F:33][C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH2:36]>C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]1[N:36]([C:35]2[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=2[F:33])[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[N:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 95842-FluoroanilineHCID 24813Phosphorus oxychlorideHCID 69584562biphenyl-4-carboxylic acid N'-(2-benzyloxyacetyl) hydrazide

Produkt 1

HCID 220192303-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazoleAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To biphenyl-4-carboxylic acid N′-(2-benzyloxyacetyl)hydrazide (9.38 g) was added phosphorus oxychloride (30 ml), and stirred at 100° C. for one hour. After the reaction solution was cooled to ambient temperature, the reaction solution was concentrated under reduced pressure. To the resulting residue was added ethyl acetate, and the separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to afford an oily product. Subsequently, 2-fluoroaniline (5 ml) and p-toluenesulfonic acid·monohydrate (200 mg) were added to the resulting oily product, and stirred at 140° C. for 4 hours. After the reaction solution was cooled to ambient temperature, ethyl acetate was added to the reaction solution. The separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=3/1–1/1), to afford the entitled compound 3-benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole as pale yellow solid (6.60 g, 58%). The physico-chemical values are as follows.

Aufarbeitung

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionTo the resulting residue was added ethyl acetate
  4. washthe separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customto afford an oily product
  8. stirringstirred at 140° C. for 4 hours
  9. temperatureAfter the reaction solution was cooled to ambient temperature
  10. washThe separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=3/1–1/1)

Quellen und Nachweise

ORD-Eintrag
ord-292a0a704b9b471094fb6636feb1e86e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084164B2

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