Potassium hydroxy sulfite → 5,6-Difluoro-2-(methylsulfinyl)benzo[d]thiazole

HRID 598521

Reaction equation

HRID 598521 reaction equation
[F:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=2[CH:12]=1.[OH:14]OS([O-])=O.[K+]>CO.O>[F:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[S:9][C:8]([S:10]([CH3:11])=[O:14])=[N:7][C:6]=2[CH:12]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 448201045,6-Difluoro-2-(methylsulfanyl)-1,3-benzothiazole

Product 1

HCID 577489385,6-Difluoro-2-(methylsulfinyl)benzo[d]thiazoleYield 50.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 240 mg (1.1 mmol) 5,6-difluoro-2-methylsulfanyl-benzothiazole in 8 mL methanol under nitrogen at 0-5° C., was added drop wise a solution of 1.019 g (1.658 mmol) oxone in 4 mL water. The reaction mixture was stirred at 0° C. for 1 h. The suspension was diluted with water (10 mL). The solid was filtered, washed with water and dissolved in dichloromethane. The solution was dried over Na2SO4, filtered, concentrated in vacuo and purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 130 mg (50.6%) of the title compound as white solid. MS(m/e): 234.1 (M+H+).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. dissolutiondissolved in dichloromethane
  4. dry with materialThe solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified with flash column chromatography on silica eluting with a gradient
  8. customformed from n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-4288027199d7457fbbb185a38f17e62c
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Linked notes

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