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ChemicalBook CAS DataBase List N-[2-(Methacryloyloxy)ethyl]-N,N-dimethylbutan-1-aminium Bis(trifluoromethanesulfonyl)imide

N-[2-(Methacryloyloxy)ethyl]-N,N-dimethylbutan-1-aminium Bis(trifluoromethanesulfonyl)imide synthesis

4synthesis methods
-

Yield: 90%

Reaction Conditions:

in water at 20; for 3 h;

Steps:

2.1.2 2.2.1.1 N-(n-Butyl)-N,N-dimethyl-N-[2-(methacryloyloxy)ethyl]ammonium bis(fluorosulfonyl)imide ([C4NMA,11]FSI)
General procedure: The mixture of 2-(dimethylamino)ethyl methacrylate (DMAEMA, 10.0g, 64mmol) and a little excess of 1-bromobutane (9.7g, 70mmol) in acetone (20mL) was stirred at room temperature for 12h. Then, the acetone and unreacted 1-bromobutane were completely removed under reduced pressure, and the obtained solid was recrystallized from acetonitrile/ethyl acetate (1/2, v./v.), and dried under high vacuum at room temperature to afford the intermediate, N-(n-butyl)-N,N-dimethyl-N-[2-(methacryloyloxy)ethyl]ammonium bromide ([C4NMA,11]Br), as a solid (16.8g, 89% yield). Afterwards, the intermediate, [C4NMA,11]Br (5.0g, 17mmol), was dissolved in deionized water (60mL), and a slightly excess of KFSI (4.2g, 19mmol) was added and stirred for 3h at room temperature. The organic layer at the bottom was separated and washed with deionized water untilno more bromide anion was detected byAgNO3 solution. The liquid was rigorously dried under vacuum at room temperature for24h to afford pure product, N-(n-butyl)-N,N-dimethyl-N-[2-(methacryloyloxy)ethyl]ammonium bis(fluorosulfonyl)imide ([C4NMA,11]FSI), as a colorless oil (6.0g, 90% yield).

References:

Zhang, Heng;Li, Li;Feng, Wenfang;Zhou, Zhibin;Nie, Jin [Polymer,2014,vol. 55,# 16,p. 3339 - 3348]