2,6-Dichloropyridine → 2-Chloro-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine

HRID 443011

Reaktionsgleichung

Reaktionsgleichung von HRID 443011
[H-].[Na+].[CH3:3][N:4]1[C:8]([OH:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[N:5]1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=1>CN(C)C(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:9][C:8]2[N:4]([CH3:3])[N:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=2)[N:16]=1

Komponenten

5

Edukt 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 178481859HCID 178481859, Verbindung

Produkt 1

HCID 217146352-Chloro-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

1.8 g (71 mmol) of sodium hydride (95 percent) was suspended in 25 ml of N,N-dimethylacetamide. A solution of 12.46 g (67 mmol) of 1-methyl-5-hydroxy-3-(trifluoromethyl)pyrazole (J Heterocycl. Chem. 1990, 27, 243) in 40 ml of N,N-dimethylacetamide was added dropwise over 1 hour at 22° C. The resulting solution was added dropwise over 3 hours, under nitrogen, to a solution of 18.5 g (125 mmol) of 2,6-dichloropyridine in 37.5 ml of N,N-dimethylacetamide, heated to 135° C. After a further 5 hours of reaction time, the mixture was cooled to room temperature, the sodium chloride which had precipitated out was filtered off and the filtrate was concentrated. The residue was taken up with toluene and water and the organic phase was washed with saturated sodium chloride solution and concentrated. The solid residue was distilled under vacuum. The title compound distills at 175° C. under 25 mbar. This gave 12.5 g of crude product in the form of a yellow solid (96 percent pure, GC). This was purified by recrystallization from diisopropyl ether. The yield was 11.55 g (62 percent) of colorless crystals, content (GC): 99.9 percent. Other data concerning the product was:

Aufarbeitung

  1. customAfter a further 5 hours of reaction time
  2. temperaturethe mixture was cooled to room temperature
  3. customthe sodium chloride which had precipitated out
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated
  6. washthe organic phase was washed with saturated sodium chloride solution
  7. concentrationconcentrated
  8. distillationThe solid residue was distilled under vacuum
  9. distillationThe title compound distills at 175° C. under 25 mbar
  10. customThis was purified by recrystallization from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ed0edd7cd4ba4c5596997e0f87d0b660
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892032

Verknüpfte Notizen

Wird geladen…