m-Chloroperbenzoic acid → HCID 86628945, compound

HRID 253330Notes

Reaction equation

HRID 253330 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:8]([F: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]([F: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(Cl)(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([F: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]([F: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 86628946HCID 86628946, compound

Product 1

HCID 86628945HCID 86628945, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.9 g of [5-(5-amino-3-trifluoromethyl-1,2,4-triazolyl)-4-fluoro-2-methylphenyl]2,2,2-trifluoroethyl sulfide was dissolved in 100 ml of chloroform, and 1.0 g of m-chloroperbenzoic acid was added at 0° C., followed by stirring at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (eluent ethyl acetate:hexane:triethylamine=50:50:1) to obtain 1.8 g of [5-(5-amino-3-trifluoromethyl-1,2,4-triazolyl)-4-fluoro-2-methylphenyl]2,2,2-trifluoroethyl sulfoxide as pale yellow crystals (melting point 236 to 238° C.).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe obtained residue was purified by column chromatography (eluent ethyl acetate:hexane:triethylamine=50:50:1)

Sources & evidence

ORD record
ord-4e163f5e261b47749b5d485acae34c9e
Source dataset
uspto-grants-2011_01
Patent number
US07872036B2

Reaction notes

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