Hydrogen Peroxide → HCID 13178895, compound

HRID 1614745Notes

Reaction equation

HRID 1614745 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[O:7][CH2:8][CH2:9][NH:10][CH:11]([CH3:23])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([S:21][CH3:22])[CH:14]=1)[CH3:3].[OH:28]O>C(O)C>[ClH:1].[CH2:2]([O:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[O:7][CH2:8][CH2:9][NH:10][CH:11]([CH3:23])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([S:21]([CH3:22])=[O:28])[CH:14]=1)[CH3:3]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 13178891HCID 13178891, compound

Product 1

HCID 13178895HCID 13178895, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of ethanol was dissolved 1.0 g of 4-{2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylthio)anisole hydrochloride and then 0.5 g of an aqueous 35% hydrogen peroxide solution was added to the solution with stirring. After stirring the mixture for 18 hours at room temperature, ethanol was distilled off under reduced pressure and the remaining sticky product was dispersed in 20 ml of water and extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed three times each time each with 20 ml of water and after acidifying the solution with 0.2 ml of concentrated hydrochloric acid, the solvent was distilled off under reduced pressure. The remaining sticky material was applied to a silica gel column chromatography and eluted using a mixture of ethyl acetate and methanol (4:1 by volume ratio). The sticky product obtained was crystallized by the addition of 3 ml of isopropanol and the crystals thus formed were recovered by filtration to provide 0.4 g of 4-{2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylsulfinyl)anisole hydrochloride.

Workup

  1. stirringAfter stirring the mixture for 18 hours at room temperature
  2. distillationethanol was distilled off under reduced pressure
  3. additionthe remaining sticky product was dispersed in 20 ml of water
  4. extractionextracted with 100 ml of ethyl acetate
  5. washThe ethyl acetate layer was washed three times each time each with 20 ml of water
  6. distillationthe solvent was distilled off under reduced pressure
  7. washeluted
  8. additiona mixture of ethyl acetate and methanol (4:1 by volume ratio)
  9. customThe sticky product obtained
  10. customwas crystallized by the addition of 3 ml of isopropanol
  11. customthe crystals thus formed
  12. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-d11de06d3b1240ec8b417a8074d10cdc
Source dataset
uspto-grants-1993_03
Patent number
US05198587

Reaction notes

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