Hydrogen Peroxide → HCID 12850099, compound

HRID 1638741Notes

Reaction equation

HRID 1638741 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([NH:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([S:24][CH3:25])[CH:18]=2)[OH:16])[CH3:12])=[CH:5][CH:4]=1.[OH:26]O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([NH:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([S:24]([CH3:25])=[O:26])[CH:18]=2)[OH:16])[CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 12850096HCID 12850096, compound

Product 1

HCID 12850099HCID 12850099, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 70 ml of methanol was dissolved 2.5 g of α-{[3-(4-methoxyphenyl)-1-methylpropylamino]-methyl}-4-methyl-3-methylthiobenzenemethanol and then 8 ml of an aqueous 30% hydrogen peroxide solution was added dropwise to the solution under ice-cooling. After allowing the reaction mixture to stand overnight the at room temperature, methanol was distilled off and after adding 50 ml of water to the residue, the product was extracted with ethyl acetate. The ethyl acetate layer formed was dried by anhydrous magnesium sulfate and after distilling off the solvent, the residue was purified with a silica gel column chromatography (eluate: a mixture of benzene, ethyl acetate, and methanol (4:3:1 by volume ratio) to provide 2.0 g of the amorphous caramel-like powder of α-{[3-(4-methoxyphenyl)-1-methylpropylamino]methyl}-4-methyl-3-methylsulfinylbenzenemethanol.

Workup

  1. temperaturecooling
  2. distillationthe at room temperature, methanol was distilled off
  3. additionafter adding 50 ml of water to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. customThe ethyl acetate layer formed
  6. dry with materialwas dried by anhydrous magnesium sulfate
  7. distillationafter distilling off the solvent
  8. customthe residue was purified with a silica gel column chromatography (eluate
  9. additiona mixture of benzene, ethyl acetate, and methanol (4:3:1 by volume ratio)

Sources & evidence

ORD record
ord-12c3d68295f64a639d22e749600459cd
Source dataset
uspto-grants-1989_11
Patent number
US04880841

Reaction notes

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