Carbon Dioxide → [Chloro(dimethylamino)methylidene]-dimethylazanium chloride

HRID 1741215

Reaction equation

HRID 1741215 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH3:7][N:8]([CH3:14])[C:9](=O)[N:10]([CH3:12])[CH3:11].C(=O)=O>C(Cl)(Cl)(Cl)Cl>[Cl-:4].[CH3:7][N:8]([CH3:14])[C:9]([Cl:4])=[N+:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 12437TetramethylureaHCID 65578Oxalyl chloride

Product 1

HCID 177416803[Chloro(dimethylamino)methylidene]-dimethylazanium chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

A solution of 3.2 ml (0.037 mol) of oxalyl chloride in 30 ml of anhydrous carbon tetrachloride is added dropwise to a solution of 4.4 ml (0.037 mol) of tetramethylurea in 20 ml of anhydrous carbon tetrachloride with stirring. The reaction medium is maintained at reflux, with continued stirring, until the evolution of gases (CO and CO2) formed by the reaction has ceased. The CCl4 is than eliminated by distillation at atmospheric pressure. Tetramethylchloroformamidinium chloride is obtained in the form of a white solid (6.23 g). This solid is placed in solution at 0° C. in 40 ml of anhydrous acetonitrile.

Workup

  1. temperatureThe reaction medium is maintained
  2. customformed by the reaction
  3. distillationthan eliminated by distillation at atmospheric pressure

Sources & evidence

ORD record
ord-4babe1f3a50c4e7caea25f72c57901cf
Source dataset
uspto-grants-1999_10
Patent number
US05973080

Linked notes

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