Reaction #80267

Reaction equation

N,N-bis[2((phenoxycarbonyl)oxy)ethyl]-N-methylamine

acetonitrile

methyl p-toluenesulfonate

→

5

N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N,N-dimethylammonium p-Toluene-sulfonate

Solvents

ether

Conditions

Workup

1. 1
   OtherTo a 250 ml round-bottomed flask fitted with a reflux condenser, magnetic stirrer, and argon inlet
2. 2
   workup.ADDITIONAfter addition
3. 3
   Temperaturethe mixture is heated
4. 4
   Temperatureto reflux for 2 h
5. 5
   OtherThe product precipitates from the mixture
6. 6
   Otherdried

Procedure

To a 250 ml round-bottomed flask fitted with a reflux condenser, magnetic stirrer, and argon inlet are added N,N-bis[2((phenoxycarbonyl)oxy)ethyl]-N-methylamine (25.00 g, 69.6 mmol), acetonitrile (100 ml), and methyl p-toluenesulfonate (12.95 g, 69.6 mmol). After addition is complete, the mixture is heated to reflux for 2 h. The cooled mixture is treated with ether (500 ml). The product precipitates from the mixture and dried to give 5 as a white powder, 31.14 g (81%): mp 117°-118° C.

Source