Ammonia → 5-Bromo-6-chloropyridine-3-sulfonamide

HRID 573116Notes

Reaction equation

HRID 573116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].[NH3:13]>CO>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:13])(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

Product 1

HCID 47300225-Bromo-6-chloropyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-Bromo-6-chloropyridine-3-sulfonyl chloride (8.2 g) in methanol (20 mL) was cooled to 0° C. To this solution was added 7N NH3 in methanol (80 mL). The reaction mixture was stirred overnight. The solvent was removed at low temperature, and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel to give the product.

Workup

  1. customThe solvent was removed at low temperature
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel
  9. customto give the product

Sources & evidence

ORD record
ord-a11b05351f2d40da8332d9b9d459e610
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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