Toluene → HCID 86614377, compound

HRID 2110941Notes

Reaction equation

HRID 2110941 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[CH:2]=[CH2:3].[CH2:9]([Br:13])[CH2:10][CH2:11][CH3:12].C1(C)C=CC=CC=1>C(#N)C>[Br-:13].[CH2:9]([N+:6]1[CH:7]=[CH:8][N:4]([CH2:1][CH:2]=[CH2:3])[CH:5]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8002Butyl bromideHCID 357941-Allyl-1H-imidazole

Product 1

HCID 86614377HCID 86614377, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

1-Allylimidazole (1.0 mL: 0.009 mol) was ice-cooled, and n-butyl bromide (2.97 mL: 0.28 mol) was added thereto dropwise. After the dropwise addition, 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 100 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 24 hours. After the acetonitrile was distilled off, the viscous liquid was recovered with dichloromethane, and the solvent was distilled off. The 1-butyl-3-allylimidazolium bromide thus obtained was a liquid at room temperature, the amount collected was 1.93 g (yield; 85%), the glass transition temperature (T.g) was −62.5° C., and the ionic conductivity at 30° C. was 0.533 (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. additionAfter the dropwise addition
  3. customa viscous liquid that separated out
  4. customwas recovered
  5. customdried
  6. customThe viscous liquid thus obtained
  7. temperaturehad been heated
  8. customvacuum-dried
  9. additionwas added
  10. stirringstirring
  11. waitwas carried out for about 24 hours
  12. distillationAfter the acetonitrile was distilled off
  13. customthe viscous liquid was recovered with dichloromethane
  14. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-e11050470f664e7cb46e7836236811a5
Source dataset
uspto-grants-2009_04
Patent number
US07517999B2

Reaction notes

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