Sodium Thiosulfate → 1H-Imidazole, 5-((3,5-dimethylphenyl)sulfonyl)-1,2-dimethyl-4-(1-methylethyl)-

HRID 1857738Notes

Reaction equation

HRID 1857738 reaction equation
CC1C=C(S[C:10]2[N:14]([CH3:15])[C:13]([CH3:16])=[N:12][C:11]=2[CH:17]([CH3:19])[CH3:18])C=C(C)C=1.Cl[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27](OO)=O)[CH:22]=1.[S:31]([O-:35])([O-])(=[O:33])=S.[Na+].[Na+].[C:38](=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:38][C:21]1[CH:26]=[C:25]([S:31]([C:10]2[N:14]([CH3:15])[C:13]([CH3:16])=[N:12][C:11]=2[CH:17]([CH3:18])[CH3:19])(=[O:35])=[O:33])[CH:24]=[C:23]([CH3:27])[CH:22]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 473910HCID 473910, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 4740171H-Imidazole, 5-((3,5-dimethylphenyl)sulfonyl)-1,2-dimethyl-4-(1-methylethyl)-Yield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (6 ml) was dissolved 60 mg (0.20 mmol) of 5-(3,5-dimethylphenylthio)-4-isopropyl-1, 2-dimethyl-1H-imidazole, followed by addition of 223 mg (1.00 mmol) of 80% metachloroperbenzoic acid, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, an aqueous solution of sodium thiosulfate and then an aqueous solution of sodium hydrogen carbonate were added, and the mixture was extracted with methylene chloride. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue purified by silica gel chromatography (ethyl acetate), and recrystallized from n-hexane, to give 24 mg of Compound I-105 (yield 39%). mp 126-128° C.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue purified by silica gel chromatography (ethyl acetate)
  7. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-76c5b0b7898d468e949bc330f61ba120
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

Loading…