Methane → N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamide

HRID 1010577Notes

Reaction equation

HRID 1010577 reaction equation
[OH2:1].C.[Se](=O)=O.C([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])(=O)C.[O:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH2:26]([O:25][CH:30]([OH:1])[C:29]([C:12]1[CH:11]=[C:10]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH:9]=[CH:14][CH:13]=1)=[O:28])[CH3:27]

Participants

6

Reactant 5

HCID 297MethaneHCID 962WaterHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 3479040N-(2-acetylphenyl)benzenesulfonamide

Product 1

HCID 57429080N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamideYield 46%

Conditions

Temperature
80 °C

Procedure

1 ml of water, 1 g activated charcoal and 2.66 g (24 mmol) selenium dioxide was added to a solution of 1.65 g (6.00 mmol) N-(acetylphenyl)benzenesulphonamide in about 10 mL dioxane. The reaction mixture was stirred for approx. 4 d at 80° C. and then the solvent was eliminated using the rotary evaporator. The residue was dissolved in about 30 ml of ethanol and refluxed for approx. 4 h. The solvent was eliminated from the reaction mixture using the rotary evaporator, the residue was dissolved in about 100 mL ethyl acetate, washed about three times with 30 ml saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulphate and the solvent was eliminated using the rotary evaporator. 0.917 g (2.73 mmol, 46%) N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamide were obtained as a yellow solid.

Workup

  1. customthe rotary evaporator
  2. dissolutionThe residue was dissolved in about 30 ml of ethanol
  3. temperaturerefluxed for approx. 4 h
  4. customthe rotary evaporator
  5. dissolutionthe residue was dissolved in about 100 mL ethyl acetate
  6. washwashed about three times with 30 ml saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over sodium sulphate
  8. customthe rotary evaporator

Sources & evidence

ORD record
ord-ef6e5f3802194fe1a97537263c90f728
Source dataset
uspto-grants-2011_07
Patent number
US07977334B2

Reaction notes

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