1-Methylimidazole → HCID 178446115, compound

HRID 1604764Notes

Reaction equation

HRID 1604764 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(#N)C>[Cl-:7].[CH2:8]([N+:4]1[CH:5]=[CH:6][N:2]([CH3:1])[CH:3]=1)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 109771-Chloropentane

Product 1

HCID 178446115HCID 178446115, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Dry 1-methylimidazole (9.03 g, 0.11 mol) was mixed with 1-chloropentane (10.66 g, 0.1 mol) in a Schlenk round bottomed flask. The two components formed two layers, and acetonitrile (40 ml) was added to make the mixture homogeneous. The mixture was heated under reflux, under cover of dry nitrogen, for 5 hours. The resultant solution was allowed to cool to room temperature and evaporated to dryness in vacuo. The solid so formed was redissolved in acetonitrile (20 ml) and cooled to -13° C. for 5 days. This resulted in the formation of crystals which were isolated by Schlenk filtration and dried in vacuo for 48 hours. The yield of 1-pentyl-3-methyl imidazolium chloride was 8.2 g (69.9%), had a melting point of 58.2° C., m/z of 341. An 1H NMR spectrum of the product of this Example A1 is shown below in Tables 1 and

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux, under cover of dry nitrogen, for 5 hours
  4. customevaporated to dryness in vacuo
  5. customThe solid so formed
  6. temperaturecooled to -13° C. for 5 days
  7. customThis resulted in the formation of crystals which
  8. customwere isolated by Schlenk
  9. filtrationfiltration
  10. customdried in vacuo for 48 hours

Sources & evidence

ORD record
ord-d920858ec50b42f89ffba6d73211361c
Source dataset
uspto-grants-1999_11
Patent number
US05994602

Reaction notes

Loading…