Potassium Carbonate → 3-(5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

HRID 1172058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172058
O.[SH-].[Na+].[CH3:4][S:5]([C:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[O:10][N:9]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrC[C:29]1[C:30]([C:41]([F:44])([F:43])[F:42])=[N:31][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:33]=1[Cl:34]>CN(C)C=O.O>[Cl:34][C:33]1[N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:31]=[C:30]([C:41]([F:44])([F:43])[F:42])[C:29]=1[CH2:4][S:5][C:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[O:10][N:9]=1

Komponenten

8

Edukt 5

HCID 11430Potassium CarbonateHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 16211346Sodium hydrosulfide hydrateHCID 178628904-(Bromomethyl)-5-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazoleHCID 23689980Sodium Formaldehyde Sulfoxylate

Produkt 1

HCID 178629083-(5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazolineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.1 g of sodium hydrosulfide hydrate (purity: 70%, 26.2 mmoles) was added to a solution of 2.3 g (13.1 mmoles) of 3-methylsulfonyl-5,5-dimethyl-2-isoxazoline dissolved in 20 ml of N,N-dimethylformamide. The mixture was stirred for 2 hours. Thereto were added 1.8 g (13.1 mmoles) of anhydrous potassium carbonate, 2.0 g (13.1 mmoles) of Rongalit and 3.6 g (10.5 mmoles) of 4-bromomethyl-5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazole. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 2.7 g (yield: 65.5%) of 3-(5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as white crystals (melting point: 89 to 90° C.).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for 15 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to vacuum distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Quellen und Nachweise

ORD-Eintrag
ord-0cef064dfcdb430994da01efc41fb32e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833939B2

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