Sodium Thiosulfate → 5-(3,5-Dimethylbenzene-1-sulfinyl)-1,2-dimethyl-4-(propan-2-yl)-1H-imidazole

HRID 1857737Notes

Reaction equation

HRID 1857737 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH3:16])=[N:12][C:11]=2[CH:17]([CH3:19])[CH3:18])[CH:5]=[C:6]([CH3:8])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:28])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:8][C:6]1[CH:5]=[C:4]([S:9]([C:10]2[N:14]([CH3:15])[C:13]([CH3:16])=[N:12][C:11]=2[CH:17]([CH3:19])[CH3:18])=[O:28])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

6

Reactant 4

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

Product 1

HCID 4740165-(3,5-Dimethylbenzene-1-sulfinyl)-1,2-dimethyl-4-(propan-2-yl)-1H-imidazoleYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (10 ml) was dissolved 150 mg (0.55 mmol) of 5-(3,5-dimethylphenylthio)-4-isopropyl-1,2-dimethyl-1H-imidazole, followed by addition of 177 mg (0.82 mmol) of 80% metachloroperbenzoic acid under ice-cooling, and the mixture was stirred for 10 minutes. To the reaction mixture, an aqueous solution of sodium thiosulfate and then, an aqueous sodium hydrogen carbonate solution was added, and extracted with methylene chloride. The extract was washed with saturated brine, 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 100 mg of Compound I-104 (yield 63%). mp 100-101° C.

Workup

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

Sources & evidence

ORD record
ord-305b5adff24d4f40a1aaa2cf0a358308
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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