Ammonium Hydroxide → 5,6-Dichloropyridine-3-sulfonamide

HRID 2040251Notes

Reaction equation

HRID 2040251 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].[NH4+:13].[OH-]>C(O)(C)C>[Cl: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 14923Ammonium HydroxideHCID 47369115,6-dichloropyridine-3-sulfonyl Chloride

Product 1

HCID 47309215,6-Dichloropyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 5,6-dichloropyridine-3-sulfonyl chloride (32.16 g) in isopropyl alcohol (300 mL) at 0° C. was added a 30% aqueous solution of NH4OH (50.8 mL). After stirring overnight, the solvent was reduced to ⅓ of the original volume. It was then partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel. The material was then slurried in 1:9 ethyl acetate/hexanes, filtered and dried under vacuum to give the title compound.

Workup

  1. customIt was then partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. filtrationfiltered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-27f5c88ad0554aff8652a266caed7ef2
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

Loading…