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

HRID 2273761Notes

Reaction equation

HRID 2273761 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-4a3afdfe0504416495cd724ae9ff7d88
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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