Dimethyl sulfite → 1-Butylpyridinium methanesulfonate
Reaction equation
[Cl-].[CH2:2]([N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH: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[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5]Participants
3
Conditions
- Temperature
- 112.5 °C
Procedure
A mixture of 11.88 g (69.2 mmol) of 1-butylpyridinium chloride and 13.69 g (124.3 mmol) of dimethyl sulfite is stirred at 110-115° C. (temperature of the oil bath) for 72 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 15.51 g of 1-butylpyridinium methanesulfonate as a solid. The melting point is 91-92° C. The yield is 96.9%. The residual chloride content is less than 5 ppm. 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-e34e02bf4dea45b9b457dffac245a280
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07999111B2
Reaction notes
Loading…