Iodine → HCID 51064010, compound

HRID 1771848Notes

Reaction equation

HRID 1771848 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[I:10]I>FC(F)(F)C([O-])=O.[Ag+].ClCCCl>[NH2:1][C:2]1[C:3]([I:10])=[CH:4][C:5]([C:8]#[N:9])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 51064010HCID 51064010, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

6-Amino-3-pyridinecarbonitrile (10.0 g, 0.081 mol), silver trifluoroacetate (25.5 g, 0.115 mol) and 160 ml of 1,2-dichloroethane are combined in a flask and heated under reflux for 5 h. Iodine (29.5 g, 0.116 mol) is added, and the mixture is heated for a further 18 h. After cooling, the mixture is filtered and partitioned between water and dichloroethane. Organic and aqueous phase are filtered through Celite. The aqueous phase is extracted to exhaustion, and the combined organic phases are combined, dried and evaporated. The residue is dissolved in ethyl acetate and washed with sodium thiosulfate solution. Removal of the solvent gives 6.6 g of yellowish crystals product. These are reacted further without further purification; HPLC: 2.57 min; LCMS: 246 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 h
  3. temperaturethe mixture is heated for a further 18 h
  4. temperatureAfter cooling
  5. filtrationthe mixture is filtered
  6. custompartitioned between water and dichloroethane
  7. filtrationOrganic and aqueous phase are filtered through Celite
  8. extractionThe aqueous phase is extracted to exhaustion
  9. customdried
  10. customevaporated
  11. dissolutionThe residue is dissolved in ethyl acetate
  12. washwashed with sodium thiosulfate solution
  13. customRemoval of the solvent

Sources & evidence

ORD record
ord-42018010e37c4570884f98dfb779c517
Source dataset
uspto-grants-2016_02
Patent number
US09249140B2

Reaction notes

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