Dichloromethane → methyl N-butanimidoylcarbamate

HRID 1248101Notes

Reaction equation

HRID 1248101 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[OH-].[Na+].Cl.[C:9]([NH2:14])(=[NH:13])[CH2:10][CH2:11][CH3:12].C(Cl)Cl>O>[CH3:5][O:4][C:2]([NH:14][C:9](=[NH:13])[CH2:10][CH2:11][CH3:12])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 12828983Butanimidamide hydrochloride

Product 1

HCID 140338858methyl N-butanimidoylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

222 parts of methyl chloroformate and 337 parts of 50% strength sodium hydroxide solution are added via two inlets to a mixture of 286 parts of butyramidine hydrochloride in 1,300 parts of methylene chloride and 500 parts of water, at from 10° to 15° C., in the course of 25 minutes, while stirring. The mixture is stirred at room temperature for 2 hours, and the organic phase is separated off and concentrated on a rotary evaporator to give 320 parts (95% of theory) of N-methoxycarbonylbutyramidine of nD25 1.4763.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. customthe organic phase is separated off
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-fb794d0d9bf345cba7468b81bd50068a
Source dataset
uspto-grants-1985_06
Patent number
US04522763

Reaction notes

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