Reaction #1801

ord-68830d19234b4026807695ab721a68e9

Reaction equation

O=C=O
CO2
O=C(Cl)C(=O)Cl
oxalyl chloride
CN(C)C(=O)N(C)C
tetramethylurea
→
CN(C)C(Cl)=[N+](C)C.[Cl-]
Tetramethylchloroformamidinium chloride

Reactants

O=C=O
CO2
O=C(Cl)C(=O)Cl
oxalyl chloride
CN(C)C(=O)N(C)C
tetramethylurea

Reagents

None

Solvents

ClC(Cl)(Cl)Cl
carbon tetrachloride
ClC(Cl)(Cl)Cl
carbon tetrachloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe reaction medium is maintained
  2. 2
    Otherformed by the reaction
  3. 3
    workup.DISTILLATIONThe CCl4 is then eliminated by distillation at atmospheric pressure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726253uspto-grants-1998_03