Dichloromethane → HCID 140338860, compound

HRID 1248106Notes

Reaction equation

HRID 1248106 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH-].[Na+].Cl.[C:10]([NH2:13])(=[NH:12])[CH3:11].C(Cl)Cl>O>[CH2:5]([O:4][C:2]([NH:13][C:10](=[NH:12])[CH3:11])=[O:3])[CH3:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochloride

Product 1

HCID 140338860HCID 140338860, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

123 parts of ethyl chloroformate and 170.4 parts of 50% strength sodium hydroxide solution are added via two inlets to a mixture of 94.6 parts of acetamidine hydrochloride in 750 parts of methylene chloride and 250 parts of water, at from 10° to 15° C., in the course of 30 minutes, while stirring. After the mixture has been stirred at 25° C. for 15 minutes, the phases are separated. The aqueous phase is extracted with twice 100 parts of methylene chloride, and the solvent is removed from the organic extract to give 93.4 parts (72% of theory) of N-ethoxycarbonylacetamidine of melting point 111°-114° C.

Workup

  1. stirringAfter the mixture has been stirred at 25° C. for 15 minutes
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted with twice 100 parts of methylene chloride
  4. customthe solvent is removed from the
  5. extractionorganic extract

Sources & evidence

ORD record
ord-691ca0a8daed4b88931be109e8e7645a
Source dataset
uspto-grants-1985_06
Patent number
US04522763

Reaction notes

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