Hydrogen Peroxide → 5-{2-[2-(2-Methoxyphenoxy)-ethylamino]-1-phenylsulfinylethyl}-2-methylbenzenesulfonamide

HRID 1758447Notes

Reaction equation

HRID 1758447 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[O:5][CH2:6][CH2:7][NH:8][CH2:9][CH:10]([C:18]1[CH:19]=[CH:20][C:21]([CH3:28])=[C:22]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:23]=1)[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH:33]O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[O:5][CH2:6][CH2:7][NH:8][CH2:9][CH:10]([C:18]1[CH:19]=[CH:20][C:21]([CH3:28])=[C:22]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:23]=1)[S:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:33]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 13118104HCID 13118104, compound

Product 1

HCID 131062725-{2-[2-(2-Methoxyphenoxy)-ethylamino]-1-phenylsulfinylethyl}-2-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 20 ml of acetic acid was dissolved 2 g of 5-{2-[2-(2-methoxyphenoxy)ethylamino]-1-phenylthioethyl}-2-methylbenzenesulfonamide and after adding thereto 0.5 ml of 30% H2O2, the mixture was heated to 50°-60° C. for 3 hours. After adding thereto 100 ml of water, the reaction mixture was extracted with 200 ml of ethyl acetate. The ethyl acetate extract was washed with an aqueous 1% sodium carbonate solution and then ethyl acetate was distilled off under reduced pressure. The residue was applied to a silica gel column chromatography, the product was eluted with a mixed solvent of chloroform and methanol (9:1 by volume ratio), and the colorless viscous oily product thus obtained was crystallized by the addition of ethyl acetate. The crystals formed were recovered by filtration to provide 1.3 g of 5-{2-[2-(2-methoxyphenoxy)-ethylamino]-1-phenylsulfinylethyl}-2-methylbenzenesulfonamide.

Workup

  1. additionafter adding
  2. additionAfter adding
  3. extraction100 ml of water, the reaction mixture was extracted with 200 ml of ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with an aqueous 1% sodium carbonate solution
  6. distillationethyl acetate was distilled off under reduced pressure
  7. washthe product was eluted with a mixed solvent of chloroform and methanol (9:1 by volume ratio)
  8. customthe colorless viscous oily product thus obtained
  9. customwas crystallized by the addition of ethyl acetate
  10. customThe crystals formed
  11. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-b2b165f054524d44b2fadc7f9cd1ba27
Source dataset
uspto-grants-1983_02
Patent number
US04373106

Reaction notes

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