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

HRID 2045046Notes

Reaction equation

HRID 2045046 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 mixture 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 solid was purified by flash column chromatography on silica gel using 10-50% ethyl acetate in hexanes to give the title compound.

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 solid was purified by flash column chromatography on silica gel using 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-43513a13847247b8ae07597f6a19732d
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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