1H-1,2,4-Triazole → Metconazole

HRID 257610

Reaktionsgleichung

Reaktionsgleichung von HRID 257610
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2([OH:20])[CH2:14]OS(C)(=O)=O)=[CH:4][CH:3]=1.[NH:23]1[CH:27]=[N:26][CH:25]=[N:24]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2([OH:20])[CH2:14][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium Carbonate2×HCID 147219061-(4-Chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-methylsulphonyloxymethylcyclopentane

Produkt 1

HCID 86210Metconazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 0.22 g 1-(4-chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-methylsulphonyloxymethylcyclopentane prepared as described in Example 1 (j), 47 mg 1,2,4-triazole and 0.1 g potassium carbonate in 3 ml N-methylpyrrolidone was warmed at 50° C. for 2 hours. A further 0.1 g potassium carbonate was then added, the temperature was raised to 120° C. and the reaction continued overnight at this temperature. The reaction mixture was then partitioned between diethyl ether and water and the organic solution flashed to give 1-(4-chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-(1,2,4-triazol-1-yl)methylcyclopentane crystallised from petroleum as a single stereoisomer (Isomer A). The conversion yield of Isomer A, corrected for purity, was 72%. The structure of the product was established by n.m.r. spectroscopy. Purity of Isomer A was 90% and Isomer B was not detected.

Aufarbeitung

  1. customprepared
  2. temperaturethe temperature was raised to 120° C.
  3. customThe reaction mixture was then partitioned between diethyl ether and water

Quellen und Nachweise

ORD-Eintrag
ord-142949d75c8f4b58905fc73b4b785d3e
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262543

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