1H-1,2,4-Triazole → Tebuconazole

HRID 371487

Reaktionsgleichung

Reaktionsgleichung von HRID 371487
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:12][O:11]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH2:12][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)([OH:11])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 92571H-1,2,4-TriazoleHCID 946842-tert-Butyl-2-(2-(4-chlorophenyl)ethyl)oxirane

Produkt 1

HCID 86102TebuconazoleAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 17.9 g (0.075 mole) of 2-(4-chlorophenylethyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mole) of 1,2,4-triazole in 30 ml of ethanol was heated in a bomb tube at 150° C. for 20 hours. The reaction solution was allowed to cool and was concentrated. The residue was dissolved in ether and the solution was washed three times with water and once with sodium chloride solution, dried over sodium sulphate and concentrated. The residue was chromatographed over a silica gel column (mobile phase: methylene chloride/ethyl acetate 1:1). 12.3 g (53.2% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentane-3-ol were obtained as a viscous oil.

Aufarbeitung

  1. temperatureto cool
  2. concentrationwas concentrated
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution was washed three times with water
  5. dry with materialonce with sodium chloride solution, dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was chromatographed over a silica gel column (mobile phase: methylene chloride/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-74db8e5bb66b41c095213b112c53683b
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04532341

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