Reaktion #4308

Reaktionsgleichung

ethanol

sodium hydride

dimethyl sulfoxide

N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride

→

N-[2-[(4-Ethoxyphenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated at 120°-140° C. for 1 hr
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   SonstigeThe residue was partitioned between methylene chloride and dilute sodium hydroxide
4. 4
   TrocknenThe methylene chloride solution was dried over magnesium sulfate
5. 5
   Sonstigethe solvent was removed in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in methanol
7. 7
   workup.ADDITIONan excess of ethereal hydrogen chloride was added
8. 8
   workup.ADDITIONether was added
9. 9
   SonstigeA white solid precipitated in amount of 14.92 g (69.2%), m.p. 168°-170° C.

Vorschrift

To a suspension of 6.6 g of a 60% dispersion of sodium hydride in oil (0.165 mole) in 300 mole of dimethyl sulfoxide was added 7.5 g (0.163 mole) of absolute ethanol. The mixture was stirred at room temperature for 0.5 hr, and 20.8 g (0.080 mole) of N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride was added as a solid. The mixture was heated at 120°-140° C. for 1 hr, and the solvent was removed in vacuo. The residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in methanol, an excess of ethereal hydrogen chloride was added, and ether was added. A white solid precipitated in amount of 14.92 g (69.2%), m.p. 168°-170° C.

Quelle