Lithium N-methylmethanaminide → Hexamethylguanidinium trifluoromethanesulfonate

HRID 2116847Notes

Reaction equation

HRID 2116847 reaction equation
[CH3:1][N-:2][CH3:3].[Li+].[F:5][C:6]([F:12])([F:11])[S:7]([O-:10])(=[O:9])=[O:8].[CH3:13][N:14]([C+:16]([N:18]([CH3:20])[CH3:19])Cl)[CH3:15]>C(#N)C>[F:5][C:6]([F:12])([F:11])[S:7]([O-:10])(=[O:9])=[O:8].[CH3:13][N:14]([CH3:15])[C:16](=[N+:2]([CH3:3])[CH3:1])[N:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 5152226Lithium N-methylmethanaminideHCID 178483697HCID 178483697, compound

Product 1

HCID 87490382Hexamethylguanidinium trifluoromethanesulfonateYield 96.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.225 g (4.41 mmol) of lithium dimethylamide are added at room temperature to 1.26 g (4.42 mmol) of bis(dimethylamino)chlorocarbenium trifluoromethanesulfonate in 20 ml of acetonitrile. The reaction mixture is stirred for 12 hours, and LiCl is subsequently filtered off. The solvent is distilled off, and the residue is washed with 20 ml of diethyl ether and subsequently dried under reduced pressure (8.0 Pa), giving 1.25 g of hexamethylguanidinium trifluoromethanesulfonate, corresponding to a yield of 96.7%.

Workup

  1. filtrationLiCl is subsequently filtered off
  2. distillationThe solvent is distilled off
  3. washthe residue is washed with 20 ml of diethyl ether
  4. customsubsequently dried under reduced pressure (8.0 Pa)

Sources & evidence

ORD record
ord-b4ab3eee4bb347a7b7f357467da83eaa
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

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