Ethyl Acetate → 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(ethylsulfinylpropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

HRID 2109916Notes

Reaction equation

HRID 2109916 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[N:24]1[C:28]([N:29]([CH2:31][CH2:32][CH2:33][S:34][CH2:35][CH3:36])[CH3:30])=[C:27]([S:37]([C:40]([F:43])([F:42])[F:41])(=[O:39])=[O:38])[C:26]([C:44]#[N:45])=[N:25]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCCl>[Cl:23][C:15]1[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=[C:13]([Cl:12])[C:14]=1[N:24]1[C:28]([N:29]([CH2:31][CH2:32][CH2:33][S:34]([CH2:35][CH3:36])=[O:9])[CH3:30])=[C:27]([S:37]([C:40]([F:43])([F:42])[F:41])(=[O:38])=[O:39])[C:26]([C:44]#[N:45])=[N:25]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866002291-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

Product 1

HCID 866002301-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(ethylsulfinylpropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

m-Chloroperbenzoic acid (0.091 g, 77%, 0.4 mmol) was added to a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole (0.23 g, 0.4 mmol) in 1,2-dichloroethane at 0-5° C. The mixture was stirred at 0-5° C. for 0.5 hour, then poured into saturated sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate), evaporated and chromatographed on silica gel eluting with heptane-ethyl acetate (1/1 to 3/7) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(ethylsulfinylpropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole as a light brown oil (Compound number 2-15, 0.186 g, 71%),19F: −63.8, −78.7.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (sodium sulfate)
  3. customevaporated
  4. customchromatographed on silica gel eluting with heptane-ethyl acetate (1/1 to 3/7)

Sources & evidence

ORD record
ord-b3c0a70bfaa14c04bc5f6502e5d6d8a5
Source dataset
uspto-grants-2009_04
Patent number
US07517877B2

Reaction notes

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