Iodine → HCID 66596209, compound

HRID 1672834Notes

Reaction equation

HRID 1672834 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[OH-].[Na+].[I:14]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[I:14])#[N:2]

Participants

6

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 27513Indole-5-carbonitrile

Product 1

HCID 66596209HCID 66596209, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Cyanoindole (0.500 g, 3.52 mmol) was dissolved in DMF (25 mL), and sodium hydroxide (0.493 g, 8.79 mmol) and iodine (0.902 g, 3.55 mmol) were added thereto, then the mixture was stirred at room temperature for 25 minutes. A saturated aqueous sodium thiosulfate solution was added to the mixture, and the precipitated solid was filtered off to give 5-cyano-3-iodoindole (0.707 g, 75%).

Workup

  1. filtrationthe precipitated solid was filtered off

Sources & evidence

ORD record
ord-f9cb7c2fd22241439581aea35e1afcd9
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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