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

HRID 1247138Notes

Reaction equation

HRID 1247138 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-964dbbf9d765483b91741d676f88b888
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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