تفاعل #1269894

ord-cb2452808eb148b98e3f17211b0064ca

معادلة التفاعل

O=[N+]([O-])c1ccc(Cl)cc1CCl
4-chloro-2-chloromethyl-1-nitro-benzene
CCOC(=O)CN.Cl
glycine ethyl ester hydrochloride
CCN(CC)CC
triethylamine
CCOC(=O)CNCc1cc(Cl)ccc1[N+](=O)[O-]
title compound
المردود 99.3%
CCOC(=O)CNCc1cc(Cl)ccc1[N+](=O)[O-]
(5-Chloro-2-nitro-benzylamino)-acetic acid ethyl ester
المردود 99.3%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةwas heated
  2. 2
    درجة الحرارةat reflux for 8 h
  3. 3
    أخرىThe solvent was evaporated
  4. 4
    أخرىthe residue was triturated in warm tert-butyl methyl ether
  5. 5
    أخرىThe ammonium salts were removed by filtration
  6. 6
    تركيزthe filtrate was concentrated in vacuo

الإجراء التجريبي

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+).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08664216B2uspto-grants-2014_03