Potassium Carbonate → 3-(4-Ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline

HRID 254204

Reaktionsgleichung

Reaktionsgleichung von HRID 254204
O.[SH-].[Na+].[CH3:4][S:5]([C:8]1[CH2:12][C:11]([CH2:14][Cl:15])([CH3:13])[O:10][N:9]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrC[C:30]1[C:31]([O:40][CH2:41][CH3:42])=[N:32][CH:33]=[N:34][C:35]=1[C:36]([F:39])([F:38])[F:37]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:41]([O:40][C:31]1[C:30]([CH2:4][S:5][C:8]2[CH2:12][C:11]([CH2:14][Cl:15])([CH3:13])[O:10][N:9]=2)=[C:35]([C:36]([F:38])([F:39])[F:37])[N:34]=[CH:33][N:32]=1)[CH3:42]

Komponenten

9

Edukt 5

HCID 11430Potassium CarbonateHCID 111952063-Methylsulfonyl-5-chloromethyl-5-methyl-2-isoxazolineHCID 16211346Sodium hydrosulfide hydrateHCID 178628575-Bromomethyl-4-ethoxy-6-trifluoromethylpyrimidineHCID 23689980Sodium Formaldehyde Sulfoxylate

Produkt 1

HCID 229348943-(4-Ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazolineAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.4 g (42.3 mmoles) of sodium hydrosulfide hydrate (purity: 70%) was added into a solution of 4.6 g (21.6 mmoles) of 3-methylsulfonyl-5-chloromethyl-5-methyl-2-isoxazoline dissolved in 70 ml of DMF. The mixture was stirred for 2 hours. Then, there were added 3.0 g (21.6 mmoles) of potassium carbonate, 3.3 g (21.6 mmoles) of Rongalit and 5-bromomethyl-4-ethoxy-6-trifluoromethylpyrimidine. The mixture was stirred at room temperature for 21 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with an aqueous sodium chloride solution, followed by drying over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (solvent system: hexane-ethyl acetate) to obtain 1.9 g (yield: 30.3%) of 3-(4-ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 21 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to reduced pressure distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (solvent system: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9c5e06a7a55f4f6baaa213ad8b2a5e04
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875606B2

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