Dimethyl Sulfate → HCID 178456350, compound

HRID 1821107Notes

Reaction equation

HRID 1821107 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[CH:2]=[CH2:3].[CH3:9][O:10][S:11](=[O:15])(=O)[O:12]C>C1(C)C=CC=CC=1>[CH3:1][S:11]([O-:12])(=[O:15])=[O:10].[CH2:1]([N+:4]1[CH:8]=[CH:7][N:6]([CH3:9])[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 357941-Allyl-1H-imidazole

Product 1

HCID 178456350HCID 178456350, compoundYield 210.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 200 ml four necked flask equipped with a stirrer, a dropping funnel, a cooling tube and a thermometer, 54.07 g (0.5 mol) of 1-allyl imidazole and 50 ml of toluene were charged, to which 63.01 g (0.50 mol) of dimethyl sulfuric acid was dropped slowly taking one hour or more and reacted for 5 hours. After reaction, 114.79 g of 1-allyl-3-methyl imidazolium methyl sulfonate was obtained by drying under a reduced pressure. Then, 114.79 g of the obtained 1-allyl-3-methyl imidazolium methyl sulfonate was dissolved in 80 ml of water, and a solution in which 74.44 g of lithium hexafluoro phosphate was dissolved in 80 ml of water was added thereto at a room temperature and stirred. From separated two layers, the lower layer was fractionated and by-products were removed by adding 40 wt % of purified water and water washing five times, and vacuum drying was applied to obtain 127.37 g of 1-allyl-3-methyl imidazolium hexafluoro phosphate. As a result of ICP analysis, the total alkali metals was 2.1 ppm, chloride ion was 0.4 ppm, and each of iodide and bromide ions was 0.1 ppm or less (lower than ICP detection limit).

Workup

  1. additionwas dropped slowly
  2. waittaking one hour or more
  3. customreacted for 5 hours
  4. customAfter reaction

Sources & evidence

ORD record
ord-94e49f16cf414c2ead406f7eb1e96576
Source dataset
uspto-grants-2009_10
Patent number
US07605271B2

Reaction notes

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