Sulfuric Acid → 6-Chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 2301492Notes

Reaction equation

HRID 2301492 reaction equation
C([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:5]=1[S:14]([NH2:17])(=[O:16])=[O:15])(=O)C.Cl[Si](C)(C)C.S(=O)(=O)(O)[OH:24]>CO>[Cl:13][C:6]1[C:5]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:4]([OH:24])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6397ChlorotrimethylsilaneHCID 183734452-Acetyl-6-chloro-3-nitrobenzenesulfonamide

Product 1

HCID 112768176-Chloro-2-hydroxy-3-nitrobenzenesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-acetyl6-chloro-3-nitrobenzenesulfonamide (1.72 g, 5.83 mmol), chlorotrimethylsilane (2 mL) and fuming sulfuric acid (0.5 mL) in methanol was heated to reflux for 20 hours. The solvent was evaporated. The residue was diluted with ethyl acetate and washed with water. The organic layer was then dried (Na2SO4) and concentrated to give the desired product (1.0 g, 68%). EI-MS (m/z) 251.1, 253.2 (M−).

Workup

  1. temperatureto reflux for 20 hours
  2. customThe solvent was evaporated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was then dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-876eafb779e441418151c09417b56faa
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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