Toluene → 1,3-Dimethyl-4,5-diphenylimidazolium iodide

HRID 874171Notes

Reaction equation

HRID 874171 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[CH:3]1.[CH3:13][I:14].[C:15]1(C)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[I-:14].[CH3:1][N+:2]1[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6328Methyl iodide2×HCID 27487821-methyl-4-phenyl-1H-imidazole

Product 1

HCID 122768351,3-Dimethyl-4,5-diphenylimidazolium iodideYield 98%

Procedure

In a 25 ml one-necked flask, there is dissolved 0.240 g (1.024 mmol) of 1-methyl-4-phenylimidazole, which was obtained according to W. Collibee et al., Tetrahedron Letters (1985), 62(6), 1595-96, in 7 ml of toluene and then 100 μl of methyl iodide are added. After 15 days of heating under reflux while adding 100 μl of methyl iodide every day, the reaction medium is concentrated under reduced pressure. The residue is taken up in 50 ml of diisopropyl ether. The precipitate formed is drained, washed twice with 5 ml of diisopropyl ether, and then dried under reduced pressure. 0.370 g (98%) of 1,3-dimethyl-4,5-diphenylimidazolium iodide is thus obtained in the form of a pale yellow solid whose characteristics are the following:

Workup

  1. customwhich was obtained
  2. temperatureAfter 15 days of heating
  3. temperatureunder reflux
  4. concentrationthe reaction medium is concentrated under reduced pressure
  5. customThe precipitate formed
  6. washwashed twice with 5 ml of diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-95382193b899417d809fd827b40cd6c6
Source dataset
uspto-grants-2015_03
Patent number
US08980875B2

Reaction notes

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