Ethanol → N-Methyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 2301504Notes

Reaction equation

HRID 2301504 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([N+:13]([O-:15])=[O:14])[C:7]=1C(=O)C)(=[O:5])=[O:4].Cl[Si](C)(C)C.C([OH:26])C>S(=O)(=O)(O)O>[CH3:1][NH:2][S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([N+:13]([O-:15])=[O:14])[C:7]=1[OH:26])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 18373542N-Methyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide

Product 1

HCID 18373432N-Methyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of N-methyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide (170 mg, 0.55 mmol), 0.5 mL of chlorotrimethylsilane and 3 drops of fuming sulfuric acid in ethanol 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 (160 mg, >100%). EI-MS (m/z) 265.2, 267.2 (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-b5ccb9879309480db33328ad59ece1ca
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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