Methyl Methanesulfonate → 1,3-Dimethylimidazolium methanesulfonate

HRID 1170217Notes

Reaction equation

HRID 1170217 reaction equation
[CH3:1][S:2]([O:5]C)(=[O:4])=[O:3].[CH3:7][N+:8]1[CH:12]=[CH:11][NH:10][CH:9]=1>>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:7][N+:8]1[CH:12]=[CH:11][N:10]([CH3:1])[CH:9]=1

Participants

3

Reactant 2

HCID 4156Methyl MethanesulfonateHCID 444235HCID 444235, compound

Product 1

HCID 114128721,3-Dimethylimidazolium methanesulfonateYield 169.8%

Procedure

Methyl methanesulfonate (5.50 g; 50 mmol) was mixed with 1-methyl imidazolium (4.10 g; 50 mmol) and the reaction mixture was allowed to stand at room temperature (25° C.) for 60 hours. After this period of time, the yellow reaction mixture became solidified. The crystalline mass was crushed, washed two times with ethyl acetate and dried under vacuum, which produced colorless crystals of 1,3-dimethyl imidazolium methanesulfonate (8.16 g, 85% yield), melting point 93.1° C. RMN—1H (CDCl3) δ: 9.81 (1H, s, C—H imidazolium); 7.43 (2H, s, C—H imidazolium); 4.02 (6H, s, NCH3); 2.79 (3H, s, CH3SO3). RMN—13C (CDCl3) δ: 138.5 and 123.3 (C—H imidazolium); 39.4 (CH3SO3); 36.3 (NCH3).

Workup

  1. customto stand at room temperature
  2. custom(25° C.)
  3. customfor 60 hours
  4. waitAfter this period of time
  5. customThe crystalline mass was crushed
  6. washwashed two times with ethyl acetate
  7. customdried under vacuum, which

Sources & evidence

ORD record
ord-1da137b7806a472e96ab506c9884c9fb
Source dataset
uspto-grants-2010_11
Patent number
US07825259B2

Reaction notes

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