Hydrogen Peroxide → 4-tert-butyl-2-(phenylsulfinyl)-N-(3-sulfamoylphenyl)benzamide

HRID 79102

Reaction equation

HRID 79102 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18](=[O:21])(=[O:20])[NH2:19])[CH:13]=2)=[O:10])=[C:7]([S:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].OO.C([O-])(O)=[O:34].[Na+].C(Cl)Cl>FC(F)(F)C(O)C(F)(F)F>[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18](=[O:20])(=[O:21])[NH2:19])[CH:13]=2)=[O:10])=[C:7]([S:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:34])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 589880744-tert-butyl-2-(phenylthio)-N-(3-sulfamoylphenyl)benzamide

Product 1

HCID 589880574-tert-butyl-2-(phenylsulfinyl)-N-(3-sulfamoylphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

To a solution of 4-tert-butyl-2-(phenylthio)-N-(3-sulfamoylphenyl)benzamide (15.4 mg, 0.035 mmol) in 1,1,1,3,3,3-hexafluoropropan-2-ol (0.3 mL) was added H2O2 (30% wt in water, 0.01 mL, 0.07 mmol). The reaction was stirred at room temperature for 40 min, and saturated NaHCO3(aq) and CH2Cl2 (1 mL each) were added. The organic layer was filtered through a pad of Na2SO4 and concentrated. The product was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to give 4-tert-butyl-2-(phenylsulfinyl)-N-(3-sulfamoylphenyl)benzamide. LC/MS: m/z 457.4 (M+H)+ at 1.54 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationThe organic layer was filtered through a pad of Na2SO4
  2. concentrationconcentrated
  3. customThe product was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-81cb9df60f484fc8b8bdef8516f11b63
Source dataset
uspto-grants-2014_09
Patent number
US08841483B2

Linked notes

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