Acetic Acid → 5-Chloro-2-[(4,4-difluoro-3-buten-1-yl)sulfonyl]thiazole

HRID 1274457Notes

Reaction equation

HRID 1274457 reaction equation
OO.[Cl:3][C:4]1[S:8][C:7]([S:9][CH2:10][CH2:11][CH:12]=[C:13]([F:15])[F:14])=[N:6][CH:5]=1.C(O)(=[O:18])C.[OH-:20].[Na+]>O>[Cl:3][C:4]1[S:8][C:7]([S:9]([CH2:10][CH2:11][CH:12]=[C:13]([F:15])[F:14])(=[O:18])=[O:20])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 11128457HCID 11128457, compound

Product 1

HCID 109566895-Chloro-2-[(4,4-difluoro-3-buten-1-yl)sulfonyl]thiazoleYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Hydrogen peroxide (0.77 g) was added to a mixture of 5-chloro-2-(4,4-difluorobut-3-enylthio)thiazole (1.94 g) and glacial acetic acid (21 g) at a temperature of 55-60° C. and the resultant mixture maintained at this temperature for 6 hours. After cooling the mixture to 5° C. and adding sufficient 47% sodium hydroxide solution to adjust the pH to 6 the mixture was diluted with water (20 ml) and extracted with chloroform (3×20 ml). The combined extracts were washed with water (20 ml), sodium bisulfite solution (20 ml), and water (20 ml) and dried over anhydrous magnesium sulfate. Removal of the solvent by evaporation under reduced pressure yielded 5-chloro-2-(4,4-difluorobut-3-enylsulfonyl)thiazole (1.95 g, 82%).

Workup

  1. extractionextracted with chloroform (3×20 ml)
  2. washThe combined extracts were washed with water (20 ml), sodium bisulfite solution (20 ml), and water (20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the solvent
  5. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-f3971572bdf24b4a805e517245d10b79
Source dataset
uspto-grants-2000_12
Patent number
US06156904

Reaction notes

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