Water → 2-[3-(2,6-dichlorophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid

HRID 2240564Notes

Reaction equation

HRID 2240564 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[S:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH3:30])[CH:28]=2)[N:23]([CH2:31][C:32]([OH:34])=[O:33])[C:22]=1[CH3:35].S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:43]>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[S:20]([C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH3:30])[CH:28]=2)[N:23]([CH2:31][C:32]([OH:34])=[O:33])[C:22]=1[CH3:35])(=[O:9])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21077814{3-[(2,6-Dichlorophenyl)sulfanyl]-2,5-dimethyl-1H-indol-1-yl}acetic acid

Product 1

HCID 100472802-[3-(2,6-dichlorophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chlorobenzenecarboperoxoic acid (0.34 g) was added to a solution of the product from example 24 step a) (0.18 g) in acetonitrile (5 ml) and water (0.5 ml). The reaction was stirred for 1 h, 1M aqueous sodium thiosulphate (2 ml) added and stirred for a further 15 min. The mixture was filtered, purified by reverse phase HPLC and evaporated in vacuo to yield the title compound as a white solid (40 mg).

Workup

  1. stirringstirred for a further 15 min
  2. filtrationThe mixture was filtered
  3. custompurified by reverse phase HPLC
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb0869ec06584809b2853a9589c32c5f
Source dataset
uspto-grants-2010_05
Patent number
US07723373B2

Reaction notes

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