Lithium N-methylmethanaminide → HCID 87490914, compound

HRID 2116852Notes

Reaction equation

HRID 2116852 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].[CH3:12][N:13]([C+:15]([N:17]([CH3:19])[CH3:18])Cl)[CH3:14].[CH3:20][N-:21][CH3:22].[Li+]>C(#N)C>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].[CH3:12][N:13]([CH3:14])[C:15](=[N+:21]([CH3:22])[CH3:20])[N:17]([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 5152226Lithium N-methylmethanaminideHCID 178483688HCID 178483688, compound

Product 1

HCID 87490914HCID 87490914, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.50 g (4.89 mmol) of bis(dimethylamino)chlorocarbenium tosylate and 0.25 g (4.90 mmol) of lithium dimethylamide are dissolved in 15 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 1.49 g of hexamethylguanidinium tosylate, corresponding to a yield of 96.6%.

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-833f2e33f0ae45de95a8a3a577fa0fc6
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

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