Methanol → 4-{2-[2-(2-Methoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylsulfinyl)anisole

HRID 1614744Notes

Reaction equation

HRID 1614744 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH2:6][CH2:7][NH:8][CH:9]([CH3:21])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([S:19][CH3:20])[CH:12]=1.[Na].C[OH:28]>O>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH2:6][CH2:7][NH:8][CH:9]([CH3:21])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([S:19]([CH3:20])=[O:28])[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 131788884-{2-[2-(2-Methoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylthio)anisole

Product 1

HCID 131788924-{2-[2-(2-Methoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylsulfinyl)anisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 100 ml of a mixture of methanol and water (5:1) was dissolved 1.8 g of 4-{2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylthio)anisole and after adding dropwise thereto 10.5 ml of an aqueous solution of 0.5M sodium metaperoiodate at 0° C., the mixture was stirred overnight at 4° C. The crystals formed were removed by filtration and the filtrate was concentrated under reduced pressure and the residue formed was purified by a silica gel column chromatography (eluate: a mixture of chloroform and methanol (97:3 by volume ratio) to provide 722 mg of oily 4-{2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylsulfinyl)anisole. The product was dissolved in 10 ml of methanol and after adding thereto a solution of 252 mg of oxalic acid di-hydrate dissolved in 6 ml of methanol, the mixture was allowed to stand overnight at room temperature. The resulting crystalline material was recovered by filtration and recrystallized from ethanol to provide 700 mg of 4-{2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl}-2-(methylsulfinyl)anisole oxalate having a melting point of 172°-174° C. The product has the following physicochemical properties:

Workup

  1. additionafter adding dropwise
  2. customThe crystals formed
  3. customwere removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue formed
  6. customwas purified by a silica gel column chromatography (eluate
  7. additiona mixture of chloroform and methanol (97:3 by volume ratio)

Sources & evidence

ORD record
ord-0a3d7de60104406faa9b8f1c4df4983c
Source dataset
uspto-grants-1993_03
Patent number
US05198587

Reaction notes

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