Dimethyl sulfite → 1-Butyl-1-methylpyrrolidin-1-ium methanesulfonate
Reaction equation
[Cl-].[CH2:2]([N+:6]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5].[S:12]([O:16]C)([O:14]C)=[O:13]>>[CH3:2][S:12]([O-:16])(=[O:14])=[O:13].[CH2:2]([N+:6]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]Participants
Conditions
- Temperature
- 112.5 °C
Procedure
A mixture of 11.20 g (63.0 mmol) of 1-butyl-1-methylpyrrolidinium chloride and 13.0 g (118.0 mmol) of dimethyl sulfite is stirred at 110-115° C. (temperature of the oil bath) for 48 hours under an inert-gas atmosphere (nitrogen) in a sealed reaction vessel with pressure valve for 1-1.5 bar above atmospheric pressure. The end of the reaction is determined by NMR measurement. The product is pumped off over the course of 5 hours in vacuo at 13.3 Pa and 115° C. (temperature of the oil bath), giving 14.9 g of 1-butyl-1-methylpyrrolidinium methanesulfonate as a solid. The melting point is 59-60° C. The residual chloride content is less than 5 ppm. The yield is virtually quantitative. The product is investigated by means of NMR spectroscopy.
Workup
- customin a sealed reaction vessel with pressure valve for 1-1.5 bar above atmospheric pressure
- customis pumped off over the course of 5 hours in vacuo at 13.3 Pa and 115° C.
Sources & evidence
- ORD record
- ord-7a4425a7c2c847c08cc82894cf79be16
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07999111B2
Reaction notes
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