Hydrogen Peroxide → 3-Chloro-2-pyridinesulfonamide-1-oxide

HRID 414036Notes

Reaction equation

HRID 414036 reaction equation
[Cl:1][C:2]1[C:3]([S:8]([NH2:11])(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:12]O>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:12])[C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 146531913-Chloropyridine-2-sulfonamide

Product 1

HCID 146531923-Chloro-2-pyridinesulfonamide-1-oxide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirring solution of 3-chloro-2-pyridinesulfonamide (2.5 g, 13.0 mmol) in 35 mL of trifluoroacetic acid was added 30% H2O2 (1.2 g, 35.1 mmol). The solution was concentrated to ~15 mL, diluted with ethyl acetate, washed twice with brine, dried and concentrated. The resulting solid was flash chromatographed with EtOAc to afford the desired product, m.p. 195°-197° C.

Workup

  1. concentrationThe solution was concentrated to ~15 mL
  2. additiondiluted with ethyl acetate
  3. washwashed twice with brine
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed with EtOAc

Sources & evidence

ORD record
ord-f666cba1e83b4b27a01b856d53dc4028
Source dataset
uspto-grants-1988_12
Patent number
US04789465

Reaction notes

Loading…