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

HRID 254204Notes

Reaction equation

HRID 254204 reaction equation
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]

Participants

9

Reactant 5

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

Product 1

HCID 229348943-(4-Ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazolineYield 30.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9c5e06a7a55f4f6baaa213ad8b2a5e04
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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