Iodine → 3-Iodo-5-(trifluoromethyl)pyridin-2-amine

HRID 931044Notes

Reaction equation

HRID 931044 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[I:12]I.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>S([O-])([O-])(=O)=O.[Ag+].[Ag+].C(O)C>[I:12][C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 153509143-Iodo-5-(trifluoromethyl)pyridin-2-amineYield 67.1%

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 5-(trifluoromethyl)pyridin-2-amine (12.0 g), silver(I) sulfate (23.1 g) and ethanol (400 mL) was added iodine (37.6 g) in several parts at room temperature, and the reaction mixture was stirred overnight at room temperature. To the reaction solution was added saturated aqueous sodium thiosulfate solution, and the mixture was stirred for 30 min, and neutralize with 1N aqueous sodium hydroxide solution. The insoluble substance was removed by filtration, the filtrate was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (14.3 g).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe insoluble substance was removed by filtration
  3. extractionthe filtrate was extracted with ethyl acetate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8751789e30b74727a3c0c14de9435ebe
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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