Acetic Acid → 6-(5-(Methylsulfonyl)-1,3,4-thiadiazol-2-yl)benzo[d]isothiazole

HRID 2075384Notes

Reaction equation

HRID 2075384 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]2[CH:16]=[CH:15][C:11]3[CH:12]=[N:13][S:14][C:10]=3[CH:9]=2)=[N:5][N:4]=1.OO.CC(O)=[O:21].[OH2:23]>C([O-])(O)=O.[Na+].CCOC(C)=O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][S:2]([C:3]1[S:7][C:6]([C:8]2[CH:16]=[CH:15][C:11]3[CH:12]=[N:13][S:14][C:10]=3[CH:9]=2)=[N:5][N:4]=1)(=[O:21])=[O:23]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 670892736-(5-(Methylthio)-1,3,4-thiadiazol-2-yl)benzo[d]isothiazole

Product 1

HCID 670893666-(5-(Methylsulfonyl)-1,3,4-thiadiazol-2-yl)benzo[d]isothiazole

Reagents, catalysts & solvents 3

HCID 26052Sodium tungstateCatalystHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)benzo[d]isothiazole (0.20 g, 0.75 mmol) and hydrogen peroxide (0.19 mL, 1.9 mmol) in AcOH (2.00 mL, 35 mmol) was added sodium tungstate (0.0026 mL, 0.038 mmol). The resulting mixture was stirred at room temperature 16 hours. The mixture was diluted with aqueous NaHCO3 (10 mL), water (10 mL) and EtOAc (5 mL). The separated aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the product as a residue which was used without further purification.

Workup

  1. extractionThe separated aqueous layer was extracted with EtOAc (2×10 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the product as a residue which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-205c70a747cc403b852b076a86733cd7
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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