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1H-1,2,4-Triazole → 1,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

HRID 371181
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 371181
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=3)[CH2:10][O:9]2)=[N:6][CH:7]=1.[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)([OH:9])[CH2:10][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[N:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 202745202,2-Bis(5-chloro-pyrid-2-yl)oxirane

Produkt 1

HCID 202745161,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanolAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2,2-Bis(5-chloro-pyrid-2-yl)oxirane (0.8 g), 1,2,4-triazole (1.0 g) and anhydrous potassium carbonate (3.0 g) were stirred in dry N,N-dimethylformamide (30 ml) and the mixture was heated at 85° C. for 1.5 hours. The solvent was then evaporated under vacuum, with the addition of xylene to remove final traces of N,N-dimethylformamide as an azeotrope, and the residue was dissolved in water (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried over megnesium sulfate and evaporated. The residue was chromatographed on silica, eluting with ethyl acetate. Evaporation of the relevant fractions gave a viscous oil which solidified on trituration with petroleum ether (b.p. 60°-80° C.). Recrystallization from hexane gave the title compound as white crystals (0.48 g, 38%) m.p. 98°-100° C.

Aufarbeitung

  1. customThe solvent was then evaporated under vacuum, with the addition of xylene
  2. customto remove final traces of N,N-dimethylformamide as an azeotrope
  3. dissolutionthe residue was dissolved in water (20 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over megnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with ethyl acetate
  9. customEvaporation of the relevant fractions
  10. customgave a viscous oil which
  11. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-c02b2df88220435082c29a8f87cc9513
Quelldatensatz
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04529799

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