Potassium Carbonate → 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

HRID 854136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854136
[CH2:1]([S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=O)=O)[CH3:2].[SH-].[Na+].C(=O)([O-])[O-].[K+].[K+].BrCC1[C:24]([C:33]([F:36])([F:35])[F:34])=[N:25][N:26]([CH3:32])[C:27]=1[O:28][CH:29]([F:31])[F:30]>CN(C)C=O.O>[F:31][CH:29]([F:30])[O:28][C:27]1[N:26]([CH3:32])[N:25]=[C:24]([C:33]([F:34])([F:35])[F:36])[C:2]=1[CH2:1][S:3][C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 117228384-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazoleHCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazoline

Produkt 1

HCID 116174263-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazolineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6.7 g (35.0 mmol) of 3-ethanesulfonyl-5,5-dimethyl-2-isoxazoline in 50 ml of N,N-dimethylformamide was added 5.6 g (purity: 70%, 70.0 mmol) of sodium hydrosulfide, followed by 1 hour of stirring at room temperature. Thereafter, 4.8 g (35.0 mmol) of potassium carbonate and 10.8 g (35.0 mmol) of 4-bromomethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole were added thereto, followed by stirring at room temperature overnight. After the completion of the reaction was confirmed, the reaction solution was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with water and saline and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel column chromatography to obtain 7.3 g (yield: 57.9%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as white crystals (melting point: 39 to 40° C.).

Aufarbeitung

  1. stirringby stirring at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e4b32ddd01954ddb871abe5de2bf8a8e
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256298B2

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