Pyridine → N-cyclohexyl-N-methylcarbamoyl chloride

HRID 1856754Notes

Reaction equation

HRID 1856754 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][NH:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:13][N:14]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:2]([Cl:1])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7514N-MethylcyclohexylamineHCID 94429Triphosgene

Product 1

HCID 15209947N-cyclohexyl-N-methylcarbamoyl chlorideYield 295.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of triphosgene (4.35 g) in toluene (70 ml) is added dropwise N-methylcyclohexylamine (5 g). To the mixture is added dropwise pyridine (3.5 g), and the mixture is refluxed for 4 hours. The mixture is allowed to cool, and the organic layer is separated, washed with 0.1 N hydrochloric acid, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent to give N-methyl-N-cyclohexylaminocarbonyl chloride (7.62 g) as a colorless oil.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureto cool
  3. customthe organic layer is separated
  4. washwashed with 0.1 N hydrochloric acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-ba48f764b3924ae791455ee536f35cfe
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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