Sodium periodate → 3-(4-Methanesulfinyl-3-trifluoromethylphenyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 2356674Notes

Reaction equation

HRID 2356674 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]1([CH3:27])[NH:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[C:9]1=[O:26]>O.O1CCCC1>[CH3:21][S:20]([C:17]1[CH:18]=[CH:19][C:14]([N:10]2[C:9](=[O:26])[C:8]([CH3:27])([CH3:7])[NH:12][C:11]2=[O:13])=[CH:15][C:16]=1[C:22]([F:25])([F:24])[F:23])=[O:2]

Participants

5

Reactant 2

HCID 23667635Sodium periodate2×HCID 578292535,5-Dimethyl-3-(4-methylsulfanyl-3-trifluoromethylphenyl)-imidazolidine-2,4-dione

Product 1

HCID 578292573-(4-Methanesulfinyl-3-trifluoromethylphenyl)-5,5-dimethylimidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

470 mg of sodium periodate were dissolved in 5 ml of water and admixed slowly with 640 mg of 114.1, dissolved in 10 ml of tetrahydrofuran, with ice bath cooling. The mixture was stirred at room temperature overnight. Another 210 mg of sodium periodate were added and the mixture was stirred for a further 8 h. Thereafter, the reaction mixture was admixed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The chromatographic purification (silica gel; 96/4 dichloromethane/methanol) afforded 3-(4-methanesulfinyl-3-trifluoromethylphenyl)-5,5-dimethylimidazolidine-2,4-dione (114.1a). Molecular weight 334.05 (C13H13F3N2O3S); retention time Rt=1.69 min. [B]; MS (ES−): 335.19 (M−H+).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for a further 8 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe chromatographic purification (silica gel; 96/4 dichloromethane/methanol)

Sources & evidence

ORD record
ord-8b05891dc12845c8b51229a61d73341b
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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