Réaction #53929

Équation de réaction

trans-4-(5-Bromo-pentyl)-cyclohexylammonium bromide

4-(trifluoromethyl)benzenesulfonylchloride

Hünig's base

→

trans-N-[4-(5-Bromo-pentyl)-cyclohexyl]-4-trifluoromethyl-benzenesulfonamide

Rendement 91.0%

Solvants

CH2Cl2

KHSO4 TBME

Conditions de réaction

Traitement

1. 1
   LavageThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
2. 2
   Séchagedried over Na2SO4
3. 3
   Autreevaporated
4. 4
   Autreto give 1.38 g crude product which
5. 5
   Autrewas crystallized (CH2Cl2/hexane)

Mode opératoire

A solution of 1.0 g (3.04 mmol) of trans-4-(5-Bromo-pentyl)-cyclohexylammonium bromide in 12 ml CH2Cl2 was first cooled at 0° C., treated with 0.8 g (3.27 mmol) 4-(trifluoromethyl)benzenesulfonylchloride and then with 1.2 ml (7.01 mmol; 2.3 equivalents) of Hünig's base (during 30 min). After total 1.5 h at 0° C., the mixture was dissolved in aqueous 10% KHSO4/TBME (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 1.38 g crude product which was crystallized (CH2Cl2/hexane) to give 1.26 g (91%) of pure trans-N-[4-(5-Bromo-pentyl)-cyclohexyl]-4-trifluoromethyl-benzenesulfonamide, MS: 454 (M−H−, 1Br).

Source