1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride → HCID 17938222, compound

HRID 1795494Notes

Reaction equation

HRID 1795494 reaction equation
[Cl-].[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[N+:11]1[CH:15]=[CH:14][N:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[CH:12]=1.[S:25]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)([O-:28])(=[O:27])=[O:26].[Na+]>CO>[S:25]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)([O-:28])(=[O:27])=[O:26].[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[N+:11]1[CH:15]=[CH:14][N:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[CH:12]=1

Participants

4

Reactant 2

HCID 27342111,3-Bis(2,4,6-trimethylphenyl)imidazolium chlorideHCID 3720192Sodium 4-methylbenzenesulfonate2×

Product 1

HCID 17938222HCID 17938222, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.5 g (4.4 mmol) of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (F) in 10 ml of absolute MeOH is admixed with 0.854 g (4.4 mmol) of sodium tosylate. After the sodium tosylate has dissolved completely (magnetic stirring), the solution is evaporated under reduced pressure to a volume of about 3 ml, after which 50 ml of acetone are added. The mixture is stirred at 40° C. for two hours, the precipitated sodium chloride is filtered off and the solution is evaporated under reduced pressure to about 10 ml. After 24 hours, the white crystals which have precipitated are filtered off and washed with 5 ml of acetone and dried under reduced pressure. The yield is 1.9 g (90%). M=476.63 g/mol. This method of double decomposition can be used to replace the chloride anion by various other anions, for example carboxylate anions.

Workup

  1. customthe solution is evaporated under reduced pressure to a volume of about 3 ml
  2. additionafter which 50 ml of acetone are added
  3. stirringThe mixture is stirred at 40° C. for two hours
  4. filtrationthe precipitated sodium chloride is filtered off
  5. customthe solution is evaporated under reduced pressure to about 10 ml
  6. customthe white crystals which have precipitated
  7. filtrationare filtered off
  8. washwashed with 5 ml of acetone
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-a0fe60073195417c94def38a354316b9
Source dataset
uspto-grants-2006_04
Patent number
US07026523B2

Reaction notes

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