Hydrogen Peroxide → HCID 19754553, compound

HRID 1588799Notes

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[CH:17]=[C:16]([S:18][C:19]([F:22])([F:21])[F:20])[N:15]=[C:14]1[Cl:23].[OH:24]O>FC(F)(F)C(O)=O>[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[CH:17]=[C:16]([S:18]([C:19]([F:22])([F:21])[F:20])=[O:24])[N:15]=[C:14]1[Cl:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 800 mg (1.93 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-chloro-4-trifluoromethylsulfenylimidazole in trifluoroacetic acid was added 0.20 ml of 30% hydrogen peroxide at 0° C. The resulting mixture was stirred at 0° C. for 4 h and then at RT for 50 h. The mixture was evaporated at RT and the residue was partitioned between methylene chloride and a saturated aqueous sodium bisulfite solution. The organic layer was washed with an aqueous sodium bicarbonate solution and the organic layer was evaporated. The residue was purified by flash column chromatography on silica gel using 5% ethyl acetate in hexane. After the solvent was removed there was obtained 300 mg (36.02% yield) of the desired product as a white solid, mp 147.5° C.

Workup

waitat RT for 50 h
customThe mixture was evaporated at RT
customthe residue was partitioned between methylene chloride
washThe organic layer was washed with an aqueous sodium bicarbonate solution
customthe organic layer was evaporated
customThe residue was purified by flash column chromatography on silica gel using 5% ethyl acetate in hexane
customAfter the solvent was removed there

Sources & evidence

ORD record: ord-21397bf54c6f47468ea6911d0d36295a
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05223525

Reaction notes

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