m-Chloroperbenzoic acid → HCID 178510674, compound

HRID 413753Notes

Reaction equation

HRID 413753 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[C:15]([C:24]#[N:25])=[N:14]1.ClC1C=CC=C(C(OO)=[O:34])C=1.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([S:19]([C:20]([F:23])([F:21])[F:22])=[O:34])[C:15]([C:24]#[N:25])=[N:14]1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178510673HCID 178510673, compound

Product 1

HCID 178510674HCID 178510674, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 15 g (35.5 mmol) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfenyl-5-hydroxypyrazole in 125 ml of dichloromethane at room temperature was added a solution of m-chloroperbenzoic acid (8.76 g, 70%, 35.5 mmol) in 375 ml of dichloromehane. The resulting solution was stirred at room temperature for 17 hr. It was then concentrated and triturated with ethyl acetate and heptane (1:2). Upon filtration a solid was obtained. This solid was dissolved in ethyl acetate and stirred with saturated sodium bicarbonate solution. Ther layers were separated and the aqueous layer was extracted with three times of ethyl acetate. The combined organic layer was dried (magnesium sulfate) and concentrated. Upon chromatographic purification via silica gel column, a solid (5.7 g, 13.01 mol, 37%) was obtained as the desired product, mp 185-187d.

Workup

  1. concentrationIt was then concentrated
  2. customtriturated with ethyl acetate and heptane (1:2)
  3. filtrationUpon filtration a solid
  4. customwas obtained
  5. customTher layers were separated
  6. extractionthe aqueous layer was extracted with three times of ethyl acetate
  7. dry with materialThe combined organic layer was dried (magnesium sulfate)
  8. concentrationconcentrated
  9. customUpon chromatographic purification via silica gel column

Sources & evidence

ORD record
ord-41c10ab3329b4462ae795345331293ca
Source dataset
uspto-grants-2003_05
Patent number
US06569886B2

Reaction notes

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