Triethylamine → Ethyl (5-chloro-2-nitrobenzyl)aminoacetate

HRID 1965996Notes

Reaction equation

HRID 1965996 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH2:11]Cl)[CH:3]=1.Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C(N(CC)CC)C>C(O)C>[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH:19][CH2:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 125959704-Chloro-2-(chloromethyl)-1-nitrobenzene

Product 1

HCID 67363323Ethyl (5-chloro-2-nitrobenzyl)aminoacetateYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-2-chloromethyl-1-nitro-benzene (85 g, 0.41 mol), glycine ethyl ester hydrochloride (70 g, 0.50 mol) and triethylamine (121.4 ml, 0.8665 mol) in ethanol (1000 ml) was heated at reflux for 8 h. The solvent was evaporated and the residue was triturated in warm tert-butyl methyl ether. The ammonium salts were removed by filtration and the filtrate was concentrated in vacuo to give the title compound (111 g, 99%) as an amorphous brown solid which was used in the next step without purification. MS m/e: 273 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. customThe solvent was evaporated
  4. customthe residue was triturated in warm tert-butyl methyl ether
  5. customThe ammonium salts were removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa544fa0444c40e582ceab8195598ed7
Source dataset
uspto-grants-2013_04
Patent number
US08420633B2

Reaction notes

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