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

HRID 275111Notes

Reaction equation

HRID 275111 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 subjected to 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-bbf66e0e676e48bb971ece403c728daf
Source dataset
uspto-grants-1995_02
Patent number
US05391825

Reaction notes

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