Lithium N-methylmethanaminide → 1,3-Dimethyl-2-dimethylaminoimidazolidinium nitrate

HRID 2116856Notes

Reaction equation

HRID 2116856 reaction equation
[N+:1]([O-:4])([O-:3])=[O:2].[CH3:5][NH+:6]1[CH2:10][CH2:9][N:8]([CH3:11])[CH:7]1Cl.[CH3:13][N-:14][CH3:15].[Li+]>C(#N)C>[N+:1]([O-:4])([O-:3])=[O:2].[CH3:5][NH+:6]1[CH2:10][CH2:9][N:8]([CH3:11])[CH:7]1[N:14]([CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 5152226Lithium N-methylmethanaminideHCID 693110371,3-Dimethyl-2-chloroimidazolidinium nitrate

Product 1

HCID 693123831,3-Dimethyl-2-dimethylaminoimidazolidinium nitrateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.00 g (15.34 mmol) of 1,3-dimethyl-2-chloroimidazolidinium nitrate and 0.78 g (15.29 mmol) of lithium dimethylamide are dissolved in 20 ml of acetonitrile under a protective-gas atmosphere (argon). The reaction mixture is stirred for 5 hours at room temperature, and LiCl is subsequently filtered off. The salt LiCl is washed with 5 ml of acetonitrile, and the organic phases are combined. The solvent is distilled off, and the residue is dried under reduced pressure at 7 Pa and 50° C., giving 2.91 g of 1,3-dimethyl-2-dimethylaminoimidazolidinium nitrate as a liquid, corresponding to a yield of 92.2%.

Workup

  1. filtrationLiCl is subsequently filtered off
  2. washThe salt LiCl is washed with 5 ml of acetonitrile
  3. distillationThe solvent is distilled off
  4. customthe residue is dried under reduced pressure at 7 Pa and 50° C.

Sources & evidence

ORD record
ord-5ffac93d34464dd4ac156e277a65eff1
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

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