Dimethyl Sulfate → 1-Ethyl-3-methylimidazolium 2-(2-Methoxyethoxy)ethyl Sulfate

Reaction equation

[S:1]([O:6][CH3:7])([O:4][CH3:5])(=[O:3])=[O:2].C([C:10]1[NH:11][CH:12]=[CH:13][N:14]=1)C.[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21]O>>[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:7][O:6][S:1]([O-:4])(=[O:2])=[O:3].[CH3:5][N+:14]1[CH:13]=[CH:12][N:11]([CH2:20][CH3:21])[CH:10]=1

Participants

Reactant 3

HCID 6497Dimethyl Sulfate

HCID 8134Diethylene Glycol Monomethyl Ether

HCID 661302-Ethylimidazole

Product 1

HCID 121494541-Ethyl-3-methylimidazolium 2-(2-Methoxyethoxy)ethyl Sulfate

Procedure

In a 100 ml Schlenk flask, 16.27 g (0.129 moles) of dimethyl sulfate was slowly added dropwise to 12.40 g (0.129 moles) of ethylimidazole with ice cooling and under a blanket gas. Stirring of the mixture was continued at room temperature over night. After the addition of 30.92 g (0.258 moles; 2 equ.) of diethylene glycol monomethyl ether, the volatile fractions were removed in a distillation apparatus at 160° C. for 5 hours. After drying the mixture in a high vacuum, 1-methyl-3-ethylimidazolium 2-(2-methoxyethoxy)ethyl sulfate was obtained as a low-viscous, slightly yellow liquid in quantitative yield.