Réaction #1929018

Équation de réaction

water

diethylenetriamine

p-toluenesulfonyl chloride

→

desired product

tris(p-toluenesulfonyl)diethylenetriamine

Solvants

pyridine

pyridine

Conditions de réaction

Traitement

1. 1
   Autretransferred under warm conditions to an erlenmeyer flask
2. 2
   AutreAfter returning to ambient temperature
3. 3
   workup.WAITThe mixture is left
4. 4
   workup.STIRRINGstirring overnight at ambient temperature
5. 5
   workup.WAITis then placed in an ice bath for 2 hours
6. 6
   FiltrationThe orange solid which then forms is filtered off
7. 7
   Lavagewashed with cold (0° C.) 95% ethanol
8. 8
   AutreAfter drying under vacuum at 40° C.
9. 9
   Autre(rotary evaporator)

Mode opératoire

115 g (0.6 mol) of p-toluenesulfonyl chloride are dissolved in 250 ml of pyridine at ambient temperature. A solution of diethylenetriamine (21.5 ml, 0.2 mol) in pyridine (30 ml) is added dropwise. The reaction mixture is stirred at 50° C. for 90 minutes and then transferred under warm conditions to an erlenmeyer flask. After returning to ambient temperature, 200 ml of water are added. The mixture is left stirring overnight at ambient temperature and is then placed in an ice bath for 2 hours. The orange solid which then forms is filtered off and washed with cold (0° C.) 95% ethanol. After drying under vacuum at 40° C. (rotary evaporator), the desired product is obtained in the form of a light yellow solid (92 g, yield 81%).

Source