Iodine → 2-amino-N-(5-chloropyridin-2-yl)-5-iodobenzamide

HRID 1883039Notes

Reaction equation

HRID 1883039 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1.[I:18]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:16][C:11]1[CH:12]=[CH:13][C:14]([I:18])=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:17]

Participants

5

Reactant 2

HCID 807IodineHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 219063772-amino-N-(5-chloropyridin-2-yl)-5-iodobenzamideYield 32.1%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To an ice cold stirring suspension of N-(5-chloropyridin-2-yl)-2-aminobenzamide (1.01 g, 4.09 mmol) in ethanol (80 mL) was added a mixture of iodine (1.04 g, 4.10 mmol) and silver sulfate (1.29 g, 4.09 mmol). The mixture was stirred at room temperature for 3 d and filtered. The filtrate was concentrated, partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography over silica gel, eluting with a step gradient of 5-10% ethyl acetate in dichloromethane. The chromatography product was slurried in isopropanol and filtered to give 0.49 g (32%) of an orange solid.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography over silica gel
  9. washeluting with a step gradient of 5-10% ethyl acetate in dichloromethane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-151eb0e0717543488b8489e710df3e07
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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