Water → 5-[3-chloro-4-(3,5-dichloropyridine-2-yloxymethyl)phenyl]-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole

HRID 1940725

Reaktionsgleichung

Reaktionsgleichung von HRID 1940725
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[C:18]([Cl:24])[CH:17]=2)[N:13]([CH3:25])[N:12]=1.Cl[C:27]1[C:32]([Cl:33])=[CH:31][C:30]([Cl:34])=[CH:29][N:28]=1.O>COCCOC>[Cl:24][C:18]1[CH:17]=[C:16]([C:14]2[N:13]([CH3:25])[N:12]=[C:11]([C:5]3[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:4]=3[Cl:3])[N:15]=2)[CH:21]=[CH:20][C:19]=1[CH2:22][O:23][C:27]1[C:32]([Cl:33])=[CH:31][C:30]([Cl:34])=[CH:29][N:28]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27666Pyridine, 2,3,5-trichloro-HCID 214636723-(2-chloro-6-fluorophenyl)-5-(3-chloro 4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazole

Produkt 1

HCID 214636495-[3-chloro-4-(3,5-dichloropyridine-2-yloxymethyl)phenyl]-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazoleAusbeute 28,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Sodium hydride (60%, 0.12 g) is added to 1,2-dimethoxyethane (50 ml) and a solution of 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazole (1.00 g) in 1,2-dimethoxyethane (20 ml) is added dropwise thereto at -5° C. and stirred for 20 minutes. The reaction solution is added dropwise with a solution of 2,3,5-trichloropyridine (0.60 g) in 1,2-dimethoxyethane (20 ml) at -5° C. for 10 minutes with stirring. The reaction mixture is warmed to room temperature, poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography to give 0.40 g of desired compound (melting point: 153.0°-155.0° C.).

Aufarbeitung

  1. stirringwith stirring
  2. temperatureThe reaction mixture is warmed to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5668ac5b822b41b1940eaf1a347d9ac8
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700824

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