Iodine → HCID 86623607, compound

HRID 2246710Notes

Reaction equation

HRID 2246710 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:6][CH:5]=2.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=2)[N:3]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 80599o-ChlorothiophenolHCID 86012452HCID 86012452, compound

Product 1

HCID 86623607HCID 86623607, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-methyl-5-[(methylsulfonyl)amino]-1H-indole-1-acetic acid, ethyl ester (0.31 g) and 2-chlorobenzenethiol (0.27 g) were dissolved in dimethyl formamide (3 ml) followed by addition of iodine 0.30 g) for the whole to be stirred at room temperature overnight. The mixture was poured into aqueous sodium thiosulphate (50 ml) and the resultant white precipitate collected by filtration and rinsed with water, dried under vacuum to be recrystallised from ethanol. The crystals were harvested and rinsed with isohexane and dried under vacuum to give the sub-title compound (0.20 g)

Workup

  1. filtrationthe resultant white precipitate collected by filtration
  2. washrinsed with water
  3. customdried under vacuum
  4. customto be recrystallised from ethanol
  5. washrinsed with isohexane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2d1cf42d015e4b89b7d27e5c48700ae5
Source dataset
uspto-grants-2010_03
Patent number
US07687535B2

Reaction notes

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