Dichloromethane → methyl N-propanimidoylcarbamate

HRID 1248102Notes

Reaction equation

HRID 1248102 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[OH-].[Na+].Cl.[C:9]([NH2:13])(=[NH:12])[CH2:10][CH3:11].C(Cl)Cl>O>[CH3:5][O:4][C:2]([NH:13][C:9](=[NH:12])[CH2:10][CH3:11])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 12301253Propionimidamide hydrochloride

Product 1

HCID 140338862methyl N-propanimidoylcarbamateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

298.6 parts of methyl chloroformate and 472.8 parts of 50% strength sodium hydroxide solution are added via two inlets to a mixture of 298 parts of propionamidine hydrochloride in 1,300 parts of methylene chloride and 200 parts of water, at from 20° to 25° C., in the course of 25 minutes, while stirring. The reaction mixture is stirred at 25° C. for three hours and diluted with 300 parts of water, and the phases are separated. The aqueous phase is extracted once with 200 parts of methyl chloride and the solvent is stripped off from the organic extract to give 325 parts (=91% of theory) of N-methoxycarbonylpropionamidine of melting point 87°-93° C.

Workup

  1. stirringThe reaction mixture is stirred at 25° C. for three hours
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted once with 200 parts of methyl chloride
  4. extractionorganic extract

Sources & evidence

ORD record
ord-a8eea2792b7940e3ac23df74d0de3045
Source dataset
uspto-grants-1985_06
Patent number
US04522763

Reaction notes

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