Potassium Carbonate → HCID 68768624, compound

HRID 1172087Notes

Reaction equation

HRID 1172087 reaction equation
O.[SH-].[Na+].[CH3:4][C:5]1([CH3:15])[O:9][N:8]=[C:7]([S:10]([CH2:13][CH3:14])(=O)=O)[CH2:6]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrCC1[C:31]([C:37]([F:40])([F:39])[F:38])=[N:32][N:33]([CH3:36])[C:34]=1[Cl:35]>CN(C)C=O.O>[Cl:35][C:34]1[N:33]([CH3:36])[N:32]=[C:31]([C:37]([F:40])([F:39])[F:38])[C:14]=1[CH2:13][S:10][C:7]1[CH2:6][C:5]([CH3:15])([CH3:4])[O:9][N:8]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 114259074-bromomethyl-5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazoleHCID 16211346Sodium hydrosulfide hydrateHCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazolineHCID 23689980Sodium Formaldehyde Sulfoxylate

Product 1

HCID 68768624HCID 68768624, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5.59 g of sodium hydrosulfide hydrate (purity: 70%, 69.8 mmoles) was added, at room temperature, to a solution of 6.84 g (35.8 mmoles) of 5,5-dimethyl-3-ethanesulfonyl-2-isoxazoline dissolved in 200 ml of N,N-dimethylformamide. The mixture was stirred for 1 hour. To the reaction mixture, were added 4.94 g (35.8 mmoles) of anhydrous potassium carbonate, 5.51 g (35.8 mmoles) of Rongalit and further 9.46 g (34.1 mmoles) of 4-bromomethyl-5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazole. The resulting mixture was stirred at room temperature over one night 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 in this order 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 8.97 g (yield: 80.3%) of 3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline.

Workup

  1. stirringThe resulting mixture was stirred at room temperature over one night
  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 in this order 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-0bb259f9c18946b2a9ee3cecb74c7131
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

Loading…