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1h-1,2,4-Triazole sodium salt → 4-[[2-(1h-1,2,4-Triazol-1-yl)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173513
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1173513
CS(O[CH2:6][CH2:7][N:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1)[CH2:9][C:10]([F:13])([F:12])[F:11])(=O)=O.[Na].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1>CN(C=O)C>[N:27]1([CH2:6][CH2:7][N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[CH:31]=[N:30][CH:29]=[N:28]1
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Komponenten

4

Edukt 2

HCID 454898221h-1,2,4-Triazole sodium saltHCID 866237322-[[4-Cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate

Produkt 1

HCID 875240344-[[2-(1h-1,2,4-Triazol-1-yl)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrileAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate, Example 15C (0.050 g, 0.128 mmol) and 1,2,4-triazole sodium salt (0.023 g, 0.256 mmol) in DMF (2 mL) was heated at 60° C. under N2 for 45 min. Upon cooling, the mixture was partitioned between Et2O and water. The organic phase was washed with water and the combined aqueous phases were extracted twice with Et2O. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient followed by 1-10% MeOH/EtOAc gradient) and the product was crystallized from CH2Cl2/hexanes to give the title compound as a white solid (0.038 mg, 83% yield): MS (ES) m/z 364 (M+1).

Aufarbeitung

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between Et2O and water
  3. washThe organic phase was washed with water
  4. extractionthe combined aqueous phases were extracted twice with Et2O
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient followed by 1-10% MeOH/EtOAc gradient)
  9. customthe product was crystallized from CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1e6b7ba03a114ff3b4beaf79598b3c67
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834063B2

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