Potassium Carbonate → 5,5-Dimethyl-[(4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methylthio]-2-isoxazoline

HRID 1172086Notes

Reaction equation

HRID 1172086 reaction equation
[SH-].[Na+].[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9]([CH3:12])(=O)=O)[CH2:5]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].ClC[C:28]1[C:29]([O:38][CH3:39])=[N:30][CH:31]=[N:32][C:33]=1[C:34]([F:37])([F:36])[F:35]>CN(C)C=O.O>[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9][CH2:12][C:28]2[C:29]([O:38][CH3:39])=[N:30][CH:31]=[N:32][C:33]=2[C:34]([F:36])([F:37])[F:35])[CH2:5]1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 178629155-Chloromethyl-4-methoxy-6-trifluoromethylpyrimidineHCID 23689980Sodium Formaldehyde Sulfoxylate

Product 1

HCID 686218485,5-Dimethyl-[(4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methylthio]-2-isoxazolineYield 85.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.32 g of sodium hydrosulfide (purity: 70%, 4.00 mmoles) was added, at room temperature, to a solution of 0.35 g (2.00 mmoles) of 5,5-dimethyl-3-methylsulfonyl-2-isoxazoline dissolved in 10 ml of dimethylformamide. The mixture was stirred for 2 hours. To the reaction mixture were added 0.28 g (2.00 mmoles) of anhydrous potassium carbonate, 0.31 g (2.00 mmoles) of Rongalit and 0.45 g (2.00 mmoles) of 5-chloromethyl-4-methoxy-6-trifluoromethylpyrimidine. The resulting mixture was stirred at room temperature for 2 hours to give rise to a reaction. After confirmation of 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 water and 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 to obtain 0.55 g (yield: 85.9%) of 5,5-dimethyl-[(4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methylthio]-2-isoxazoline.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter confirmation of the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution and then dried 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

Sources & evidence

ORD record
ord-618803e3eec44122a420546ba9148e2f
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

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