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

HRID 1705

Reaction equation

HRID 1705 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 TetrachlorideSolvent2×

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 then 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 O° C. in 40 ml of anhydrous acetonitrile.

Workup

  1. temperatureThe reaction medium is maintained
  2. customformed by the reaction
  3. distillationThe CCl4 is then eliminated by distillation at atmospheric pressure

Sources & evidence

ORD record
ord-68830d19234b4026807695ab721a68e9
Source dataset
uspto-grants-1998_03
Patent number
US05726253

Linked notes

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