Ethyl chloroformate → N-(2-nitrophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine

HRID 373057Notes

Reaction equation

HRID 373057 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])([O-:3])=[O:2].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 430957N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine

Product 1

HCID 19811333N-(2-nitrophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(2-nitrophenyl-N',N'-dimethylethylenediamine (1.20 g) in chloroform (25 ml) was added ethyl chloroformate (0.64 g) dropwise. The reaction mixture was stirred at room temperature for 5 hours, washed with 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution in turn and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:chloroform:methanol=10:1) to give 1.10 g of N-(2-nitrophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine.

Workup

  1. washwashed with 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution in turn
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customthe residue was purified by silica gel chromatography (eluent:chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-47d0433f99d048bab15d5f082a97a0e2
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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