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

HRID 52228

Reaktionsgleichung

Reaktionsgleichung von HRID 52228
[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[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F: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[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][N:28]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 214636723-(2-chloro-6-fluorophenyl)-5-(3-chloro 4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazole

Produkt 1

HCID 214636685-[3-chloro-4-(5-trifluoromethylpyridine-2-yloxymethyl)phenyl]-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazoleAusbeute 56,7 %

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., which is stirred for 15 minutes. To the reaction solution is added dropwise a solution of 2-chloro-5-trifluoromethyl pyridine (0.60 g) in 1,2-dimethoxyethane (20 ml) at -5° C., which is stirred for 15 minutes. 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 0.80 g of desired compound (refractive index: 1.5879).

Aufarbeitung

  1. stirringwhich is stirred for 15 minutes
  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-a21056066bc54da2b8c99c86b3cc4212
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616594

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