Water → 2-(3-(2,6-Difluorophenyl)pyrazol-1-yl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile

HRID 1107681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107681
[C:1]([CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[N:5]1)#[N:2].[H-].[Na+].[CH3:19][N:20]1[C:24]([Cl:25])=[C:23]([C:26](N2C=CC=N2)=[O:27])[C:22]([Cl:33])=[N:21]1.O>C1COCC1>[F:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([F:16])[C:9]=1[C:6]1[CH:7]=[CH:8][N:4]([C:3](=[C:26]([C:23]2[C:22]([Cl:33])=[N:21][N:20]([CH3:19])[C:24]=2[Cl:25])[OH:27])[C:1]#[N:2])[N:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 221694981-Cyanomethyl-3-(2,6-difluorophenyl)pyrazoleHCID 221695221-(1-Methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole

Produkt 1

HCID 573044512-(3-(2,6-Difluorophenyl)pyrazol-1-yl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrileAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 0.5 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole dissolved in 10 ml of THF was dropwise added to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF, at 50° C. After the resulting product was stirred for 30 minutes, a solution of 0.67 g of 1-(1-methyl-3, 5-dichloropyrazole-4-carbonyl)pyrazole dissolved in 10 ml of THF was dropwise added thereto at 50° C. and then stirred overnight at room temperature. The reaction mixture was poured into water, then extracted with ethyl acetate and washed with a small amount of water. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1 to obtain 0.52 g of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(l-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile.

Aufarbeitung

  1. additionwas dropwise added
  2. stirringat 50° C. and then stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with a small amount of water
  5. dry with materialThe resulting product was dried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1

Quellen und Nachweise

ORD-Eintrag
ord-b257077c83f940baaabf5e1d30b71c2f
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063734

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