m-Chloroperbenzoic acid → HCID 59739579, compound

HRID 1192966Notes

Reaction equation

HRID 1192966 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]1([CH3:40])[O:17][N:16]=[C:15]([S:18][CH:19]([C:24]2[C:25]([C:36]([F:39])([F:38])[F:37])=[N:26][N:27]([CH3:35])[C:28]=2[O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[C:20]([F:23])([F:22])[F:21])[CH2:14]1>ClCCl>[CH3:12][C:13]1([CH3:40])[O:17][N:16]=[C:15]([S:18]([CH:19]([C:24]2[C:25]([C:36]([F:39])([F:37])[F:38])=[N:26][N:27]([CH3:35])[C:28]=2[O:29][CH2:30][C:31]([F:32])([F:33])[F:34])[C:20]([F:23])([F:22])[F:21])=[O:6])[CH2:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59739547HCID 59739547, compound

Product 1

HCID 59739579HCID 59739579, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (mCPBA) (70% by weight) (305 mg, 1.24 mmol) was added in portions to a solution of 5,5-dimethyl-3-{2,2,2-trifluoro-1-[1-methyl-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-1H-pyrazol-4-yl]-ethylsulfanyl}-4,5-dihydro-isoxazole (190 mg, 0.41 mmol) in dichloromethane (5 ml) at room temperature. The mixture was stirred at room temperature for 18 hours. The reaction was quenched by addition of saturated aqueous sodium metabisulfite solution, followed by addition of saturated aqueous sodium hydrogencarbonate solution. The two phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: hexane/dichloromethane) to give the product (Compound No. 2.35 of Table 28) as a colourless gum (105 mg, 51% yield).

Workup

  1. customThe reaction was quenched by addition of saturated aqueous sodium metabisulfite solution
  2. additionfollowed by addition of saturated aqueous sodium hydrogencarbonate solution
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. washThe combined organic phases were washed with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel (eluent: hexane/dichloromethane)

Sources & evidence

ORD record
ord-0469ee421ae143e4b922161d89a932a0
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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