Hydrogen Peroxide → 2-Sec-butylsulfinyl-4-methylsulfonyloxy-1,3-thiazole

HRID 414255Notes

Reaction equation

HRID 414255 reaction equation
[CH:1]([S:5][C:6]1[S:7][CH:8]=[C:9]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])[N:10]=1)([CH2:3][CH3:4])[CH3:2].[OH:16]O.O.[OH-].[Na+]>C(O)(=O)C>[CH:1]([S:5]([C:6]1[S:7][CH:8]=[C:9]([O:11][S:12]([CH3:15])(=[O:13])=[O:14])[N:10]=1)=[O:16])([CH2:3][CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 13914052HCID 13914052, compound

Product 1

HCID 139140652-Sec-butylsulfinyl-4-methylsulfonyloxy-1,3-thiazoleYield 49.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.0 g of 2-sec-butylthio-4-methylsulfonyloxy-1,3-thiazole was dissolved in 15 ml of acetic acid, and 2.2 ml of 35% aqueous hydrogen peroxide was added to the solution at room temperature, followed by reaction at 30° to 40° C. for 4 hours. The reaction mixture was poured into chilled water, neutralized by 5% aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate and concentrated to obtain an oil, which was purified by silica-gel column chromatography to 2.1 g of the objective compound as a pale yellow oil (yield: 49.7%).

Workup

  1. customfollowed by reaction at 30° to 40° C. for 4 hours
  2. additionThe reaction mixture was poured
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of common salt
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto obtain an oil, which

Sources & evidence

ORD record
ord-dc4efc705ded4ed89938438e52e9c97d
Source dataset
uspto-grants-1988_12
Patent number
US04791127

Reaction notes

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