Ethyl chloroformate → N'-[(Ethoxycarbonyl)oxy]benzenecarboximidamide

HRID 2263357Notes

Reaction equation

HRID 2263357 reaction equation
[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11](Cl)(=[O:15])[O:12][CH2:13][CH3:14]>C(Cl)(Cl)Cl>[CH2:13]([O:12][C:11]([O:10][N:9]=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH2:8])=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 69186N'-Hydroxybenzenecarboximidamide

Product 1

HCID 71364520N'-[(Ethoxycarbonyl)oxy]benzenecarboximidamideYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of benzamide oxime (25.0 g, 184 mmol) in chloroform (250 ml) was added dropwise a solution of ethyl chlorocarbonate (8.79 ml, 92.0 mmol) in chloroform (60 ml), and the mixture was stirred at room temperature for 3 hours. Insolubles were filtered off, and then the filtrate was concentrated. The residue was recrystallized from a mixed solvent of ethanol and water to yield 18.2 g (94.8%) of the desired product.

Workup

  1. filtrationInsolubles were filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-be96a783fe704481ac60e1036c067696
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…