Reaction #324369

Reaction equation

N-[3-(dimethylamino)propyl]methacrylamide

butanesultone

acetone

methanol

→

4-sulfonatobutyl[3-(methacryloylamino)propyl]dimethylammonium

Yield 85.5%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureto cooling, to the reaction mixture
2. 2
   FiltrationThe crystals deposited were collected by filtration
3. 3
   Washthoroughly washed with acetone

Procedure

In 380 ml of acetonitrile were dissolved 130 g (0.764 mol) of N-[3-(dimethylamino)propyl]methacrylamide, 104 g of butanesultone and 234 mg of 4-hydroxy-2,2,6,6-tetramethylpiperidinoxy and the solution was heated at 70° C. for 6 hours. After allowing to cooling, to the reaction mixture were added 1,350 ml of acetone and 150 ml of methanol and the mixture was stirred at room temperature for one hour. The crystals deposited were collected by filtration and thoroughly washed with acetone to obtain 200.0 g (yield: 85%) of 4-sulfonatobutyl[3-(methacryloylamino)propyl]dimethylammonium.

Source