m-Chloroperbenzoic acid → HCID 118432011, compound

HRID 2207966Notes

Reaction equation

HRID 2207966 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]([C:13]3[CH:14]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=4)[CH:16]=[CH:17][CH:18]=3)[CH2:11][C:10]([C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]([C:13]3[CH:14]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:26])=[O:42])=[CH:21][CH:20]=4)[CH:16]=[CH:17][CH:18]=3)[CH2:11][C:10]([C:27]([F:33])([F:32])[C:28]([F:29])([F:30])[F:31])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118431884HCID 118431884, compound

Product 1

HCID 118432011HCID 118432011, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(3-Chloro-phenyl)-5-(4′-methylsulfanyl-biphenyl-3-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (127.0 mg, 0.26 mmol) prepared in Example 24 in dichloromethane (5.0 mL), was slowly added meta-chloroperbenzoic acid (77%, 69.0 mg, 0.31 mmol) at 0° C. The reaction mixture was stirred at room temperature 30 minutes, quenched with a saturated solution of sodium hydrogen carbonate, and then extracted with dichloromethane three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5, 1/1) to give 61.0 mg of the titled compound as a yellow liquid.

Workup

  1. customat 0° C
  2. customquenched with a saturated solution of sodium hydrogen carbonate
  3. extractionextracted with dichloromethane three times
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow liquid residue
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5, 1/1)

Sources & evidence

ORD record
ord-7835be9579224245862878a6850fc1f3
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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