Ethyl Acetate → alpha-((4-Chlorophenoxy)methyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol

HRID 371484

Reaktionsgleichung

Reaktionsgleichung von HRID 371484
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]2([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.C(OCC)(=O)C>C(O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([OH:9])([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:10][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 127636212-tert-Butyl-2-[(4-chlorophenoxy)methyl]oxirane

Produkt 1

HCID 123676alpha-((4-Chlorophenoxy)methyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanolAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

72.15 g (0.3 mols) of 2-(4-chlorophenoxy-methyl)-2-tert.-butyl-oxirane and 24.15 g (0.35 mole) of 1,2,4-triazole were heated under reflux in 120 ml of ethanol for 48 hours. The mixture was then concentrated, the residue was taken up in 200 ml of ethyl acetate and the ethyl acetate mixture was heated. It was then cooled in an ice bath and the solid was filtered off and rinsed with ethyl acetate. The filtrate was concentrated, the residue was dissolved in ether/hexane and the solution was gassed with hydrogen chloride. The precipitate was filtered off and rinsed with ether and the free base was obtained by adding ethyl acetate/1N sodium hydroxide solution. 60.2 g (65% of theory) of 2-(4-chlorophenoxy-methyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of melting point 84°-87° C. were obtained.

Aufarbeitung

  1. concentrationThe mixture was then concentrated
  2. temperaturethe ethyl acetate mixture was heated
  3. temperatureIt was then cooled in an ice bath
  4. filtrationthe solid was filtered off
  5. washrinsed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in ether/hexane
  8. filtrationThe precipitate was filtered off
  9. washrinsed with ether
  10. customthe free base was obtained

Quellen und Nachweise

ORD-Eintrag
ord-56b4a62bad0740eeb478a3203ff2050f
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04532341

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