Ammonia → HCID 178514683, compound

HRID 2036789Notes

Reaction equation

HRID 2036789 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[NH3:9].Cl[S:11]([OH:14])(=O)=[O:12]>>[Br:1][C:2]1[CH:3]=[C:4]([S:11]([NH2:9])(=[O:14])=[O:12])[C:5]([OH:8])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24638Chlorosulfonic acidHCID 178515818HCID 178515818, compound

Product 1

HCID 178514683HCID 178514683, compound

Procedure

A solution of 5-bromopyridin-2-ol (0.5 g, 2.8 mmol) in chlorosulfonic acid (10 mL) was heated to 150° C. for 16 h. After this time, the reaction mixture was added dropwise to a pre-cooled aqueous ammonia solution (100 mL) at 0° C. The resulting mixture was stirred for 1 h. The aqueous layer was then extracted with ethyl acetate (150 mL), dried and concentrated to yield a residue. The residue was purified by ISCO chromatography using 3% methanol in DCM to yield 5-bromo-2-hydroxypyridine-3-sulfonamide (210 mg). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.67 (br s, 1H); 8.03 (d, 1H, J=2.8 Hz); 7.98 (d, 1H, J=2.8 Hz); 7.11 (s, 1H). LCMS Method U: retention time 1.85 min; [M+1]=253.0.

Workup

  1. extractionThe aqueous layer was then extracted with ethyl acetate (150 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto yield a residue
  5. customThe residue was purified by ISCO chromatography

Sources & evidence

ORD record
ord-b84a584c10a24b5b9ab346a7cc4139d7
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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