Toluene → HCID 23154620, compound

HRID 2110945Notes

Reaction equation

HRID 2110945 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[CH:2]=[CH2:3].[CH2:9]([I:12])[CH:10]=[CH2:11].C1(C)C=CC=CC=1>C(#N)C>[I-:12].[CH2:1]([N+:4]1[CH:8]=[CH:7][N:6]([CH2:11][CH:10]=[CH2:9])[CH:5]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 11166Allyl iodideHCID 357941-Allyl-1H-imidazole

Product 1

HCID 23154620HCID 23154620, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

1-Allylimidazole (1.0 mL: 0.009 mol) was ice-cooled, and allyl iodide (2.51 mL: 0.028 mol) was added thereto dropwise. Subsequently, the temperature was gradually increased to 25° C., and subsequently stirring was carried out continuously for 24 hours. The product was a pale brown viscous liquid. This was added dropwise to 200 mL of toluene, and a viscous liquid that separated out was recovered and dried. The same procedure was repeated once more. The viscous liquid thus obtained was made into an acetonitrile solution, active carbon that had been heated and vacuum-dried was added thereto, and stirring was carried out for about 48 hours. After the acetonitrile was distilled off, the viscous liquid was recovered with dichloromethane, and the solvent was distilled off. The 1,3-diallylimidazolium iodide thus obtained was a liquid at room temperature, the amount collected was 1.81 g (yield; 71.3%), the glass transition temperature (Tg) was −68.1° C., and the ionic conductivity at 30° C. was 1.32 mS/cm. The results are given in Table 1. The structure was confirmed by 1H-NMR measurement. The results are shown below.

Workup

  1. temperaturecooled
  2. customa viscous liquid that separated out
  3. customwas recovered
  4. customdried
  5. customThe viscous liquid thus obtained
  6. temperaturehad been heated
  7. customvacuum-dried
  8. additionwas added
  9. stirringstirring
  10. waitwas carried out for about 48 hours
  11. distillationAfter the acetonitrile was distilled off
  12. customthe viscous liquid was recovered with dichloromethane
  13. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-9042becd0bae4dc894c7dca288b401fc
Source dataset
uspto-grants-2009_04
Patent number
US07517999B2

Reaction notes

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