m-Chloroperbenzoic acid → HCID 86628939, compound

HRID 253323Notes

Reaction equation

HRID 253323 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:43])=[CH:9][C:10]([CH3:42])=[C:11]([CH:13]([S:18][CH:19]([C:24]3[CH:29]=[C:28]([N:30]4[C:34]([NH2:35])=[N:33][C:32]([C:36]([F:39])([F:38])[F:37])=[N:31]4)[C:27]([Cl:40])=[CH:26][C:25]=3[CH3:41])[C:20]([F:23])([F:22])[F:21])[C:14]([F:17])([F:16])[F:15])[CH:12]=2)[N:5]=[C:4]([C:44]([F:47])([F:46])[F:45])[N:3]=1.ClC1C=CC=C(C(OO)=[O:56])C=1>C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:43])=[CH:9][C:10]([CH3:42])=[C:11]([CH:13]([S:18]([CH:19]([C:24]3[CH:29]=[C:28]([N:30]4[C:34]([NH2:35])=[N:33][C:32]([C:36]([F:39])([F:37])[F:38])=[N:31]4)[C:27]([Cl:40])=[CH:26][C:25]=3[CH3:41])[C:20]([F:21])([F:22])[F:23])=[O:56])[C:14]([F:17])([F:16])[F:15])[CH:12]=2)[N:5]=[C:4]([C:44]([F:47])([F:46])[F:45])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86628940HCID 86628940, compound

Product 1

HCID 86628939HCID 86628939, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.3 g of [5-(5-amino-3-trifluoromethyl-1,2,4-triazolyl)-4-chloro-2-methylphenyl]2,2,2-trifluoroethyl sulfide was dissolved in 80 ml of ethyl acetate, and 0.9 g (purity 75%) of m-chloroperbenzoic acid was added under cooling with ice. The mixture was stirred under cooling with ice for 2 hours, washed with an aqueous sodium thiosulfate solution and then washed with an aqueous sodium hydrogencarbonate solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crystals were washed with carbon tetrachloride to obtain 1.2 g of [5-(5-amino-3-trifluoromethyl-1,2,4-triazolyl)-4-chloro-2-methylphenyl]2,2,2-trifluoroethyl sulfoxide as white crystals (melting point 235 to 237° C.).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 2 hours
  3. washwashed with an aqueous sodium thiosulfate solution
  4. washwashed with an aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe obtained crystals were washed with carbon tetrachloride

Sources & evidence

ORD record
ord-b54093839a104d42a7b14d3a0fd8ba46
Source dataset
uspto-grants-2011_01
Patent number
US07872036B2

Reaction notes

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