Réaction #4284

Équation de réaction

N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine

sodium perborate

sodium hydroxide

→

solid

Rendement 90.6%

N-[2-[(4-Chlorophenyl)sulfinyl]ethyl]-1-methylethanamine

Rendement 90.6%

Solvants

sulfuric acid

Conditions de réaction

Traitement

1. 1
   Extractionthe basic solution was extracted with methylene chloride
2. 2
   SéchageThe methylene chloride layer was dried with magnesium sulfate
3. 3
   Autrethe solvent removed in vacuo

Mode opératoire

A solution of 15.05 g (0.066 mole) of N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine and 12.0 g (0.0779 mole) of sodium perborate in 400 ml of 1M sulfuric acid was stirred at room temperature for about 18 hr. The solution was made basic with 50% sodium hydroxide and the basic solution was extracted with methylene chloride. The methylene chloride layer was dried with magnesium sulfate and the solvent removed in vacuo to give 14.7 g of solid. Nuclear magnetic resonance analysis showed a 9 to 1 ratio of sulfoxide to sulfide. The solid was recrystallized from ether-hexane to give 12.3 g (76.4%) of the free base title compound as crystalline solid, m.p. 52.5°-53.5° C.

Source