m-Chloroperbenzoic acid → HCID 178510674, compound

HRID 2376701Notes

Reaction equation

HRID 2376701 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 6344DichloromethaneSolvent2×HCID 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 dichloromethane. 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. The layers were separated and the aqueous layer was extracted three times with 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. customThe layers were separated
  6. extractionthe aqueous layer was extracted three times with 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-c01be7d0eb5d48b199c44e4ebd3fde6d
Source dataset
uspto-grants-2008_12
Patent number
US07468381B2

Reaction notes

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