Methyl chloroformate → methyl N-(2-phenylethanimidoyl)carbamate

HRID 1248104

Reaction equation

HRID 1248104 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[OH-].[K+].Cl.[CH2:9]([C:16]([NH2:18])=[NH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O.ClCCCl>[CH3:5][O:4][C:2]([NH:18][C:16]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[NH:17])=[O:3]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 14797Potassium HydroxideHCID 124155142-Phenylethanimidamide hydrochloride

Product 1

HCID 140338859methyl N-(2-phenylethanimidoyl)carbamateYield 93%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

137.2 parts of methyl chloroformate and a solution of 162.7 parts of potassium hydroxide in 180 parts of water are added via two inlets to a mixture of 246 parts of benzylmethanamidine hydrochloride in 530 parts of 1,2-dichloroethane and 85 parts of water, at from 10° to 15° C., in the course of 35 minutes. The mixture is stirred at 25° C. for 20 minutes, the organic phase is separated off and the aqueous phase is extracted twice more with 1,2- dichloroethane. The organic extracts are concentrated to give 259.8 parts (93% of theory) of N-methoxycarbonylbenzylmethanamidine of nD25 1.5247.

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted twice more with 1,2- dichloroethane
  3. concentrationThe organic extracts are concentrated

Sources & evidence

ORD record
ord-57f5e323111041c28e2a20ddf672fbf6
Source dataset
uspto-grants-1985_06
Patent number
US04522763

Linked notes

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