Réaction #53897

Équation de réaction

trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

H2O2 Urea

phthalic anhydride

→

trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide N-oxide

Rendement 30.7%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe solution was stirred at RT
2. 2
   LavageThe mixture was washed with an aqueous solution of NaHCO3
3. 3
   Lavagethe organic phase was washed with brine
4. 4
   Séchagedried over Na2SO4

Mode opératoire

175 mg (1.86 mmol) H2O2-Urea adduct suspended in 2 ml CH2Cl2 were treated with 137 mg (0.9 mmol) phthalic anhydride. After stirring at RT for 15 min to this mixture was added 500 mg (8.4 mmol) crude trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide in 3 ml CH2Cl2 and the solution was stirred at RT. The mixture was washed with an aqueous solution of NaHCO3, the organic phase was washed with brine and dried over Na2SO4.348 mg crude trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide N-oxide were isolated as colorless oil.

Source