Water → 4-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-3-sulfamoyl-benzoic acid
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[S:21]([NH2:24])(=[O:23])=[O:22])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[OH-:25].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:33]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:33])=[O:25])=[CH:16][C:15]=2[S:21](=[O:23])(=[O:22])[NH2:24])(=[O:11])=[O:12])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 2-[2-(4-bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamide (0.3 g, 0.69 mmol) in water (12 mL) was added 2.5 M sodium hydroxide until a clear solution was obtained (˜12 mL). Potassium permanganate (0.55 g, 3.46 mmol) was added and the resulting reaction mixture was heated at 70° C. for 3 hours. The hot solution was filtered through a pad of Celite and the solids were washed with water. Solid sodium bisulfate was added to the filtrate until the pink color disappeared. The aqueous solution was treated with charcoal, filtered, and the pH was adjusted to pH˜1 using 6 M hydrochloric acid. The formed precipitate was collected by filtration, washed with water, and dried to give 0.22 g (69% yield) of the title compound.
Workup
- customwas obtained (˜12 mL)
- customthe resulting reaction mixture
- filtrationThe hot solution was filtered through a pad of Celite
- washthe solids were washed with water
- additionSolid sodium bisulfate was added to the filtrate until the pink color
- additionThe aqueous solution was treated with charcoal
- filtrationfiltered
- filtrationThe formed precipitate was collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-5ecaec6ca9154c70b5019332eea51c29
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145380B2
Reaction notes
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