Aniline → 5-Bromo-6-(phenylamino)pyridine-3-sulfonamide

HRID 930885Notes

Reaction equation

HRID 930885 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24758Sodium hydrideHCID 47300225-Bromo-6-chloropyridine-3-sulfonamide

Product 1

HCID 896563415-Bromo-6-(phenylamino)pyridine-3-sulfonamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of Example 86a (0.136 g, 0.5 mmol), aniline (0.186 g, 2.0 mmol), and 60% sodium hydride (0.12 g, 3.0 mmol) in dioxane (2 mL) was stirred and heated at 60° C. for 16 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was neutralized with 10% HCl and extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (2:3 ethyl acetate/hexanes) to give 0.095 g of the title product.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. extractionextracted with additional ethyl acetate twice
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (2:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4c667d29947749d382588a96bf0ba228
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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