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

HRID 2355238Notes

Reaction equation

HRID 2355238 reaction equation
[OH2:1].C.[Se](=O)=O.[C:6]([C:9]1[CH:10]=[C:11]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[CH3:7].[O:25]1CCO[CH2:27][CH2:26]1>>[CH2:26]([O:25][CH:7]([OH:1])[C:6]([C:9]1[CH:10]=[C:11]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)=[O:8])[CH3:27]

Participants

6

Reactant 5

HCID 297MethaneHCID 962WaterHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 738634N-(3-acetylphenyl)benzenesulfonamide

Product 1

HCID 57429080N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamide

Conditions

Temperature
80 °C

Procedure

1 ml of water, 1 g activated charcoal and 2.66 g (24 mmol) selenium dioxide are added to a solution of 1.65 g (6 mmol) N-(3-acetyl-phenyl)-benzenesulphonamide in 10 ml dioxane. The reaction mixture is stirred for 4 days at 80° C. and then concentrated by evaporation in the rotary evaporator. The residue is dissolved in 30 ml of ethanol and refluxed for 4 hours. Then the reaction mixture is concentrated by evaporation in the rotary evaporator. The residue is dissolved in 100 ml of ethyl acetate, washed several times with 30 ml saturated, aqueous sodium hydrogen carbonate solution, dried on sodium sulphate and again concentrated by evaporation in the rotary evaporator. The crude product thus obtained as a yellow solid is reacted further without any further purification.

Workup

  1. concentrationconcentrated by evaporation in the rotary evaporator
  2. dissolutionThe residue is dissolved in 30 ml of ethanol
  3. temperaturerefluxed for 4 hours
  4. concentrationThen the reaction mixture is concentrated by evaporation in the rotary evaporator
  5. dissolutionThe residue is dissolved in 100 ml of ethyl acetate
  6. washwashed several times with 30 ml saturated
  7. dry with materialaqueous sodium hydrogen carbonate solution, dried on sodium sulphate
  8. concentrationagain concentrated by evaporation in the rotary evaporator

Sources & evidence

ORD record
ord-72f9a18a817b4c1c844f32f6b41f310f
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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