Ethanolamine → N~1~,N~3~-Bis(2-hydroxyethyl)-5-nitrobenzene-1,3-dicarboxamide

HRID 898082Notes

Reaction equation

HRID 898082 reaction equation
CO[C:3](=[O:17])[C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:6]([C:7]([O:9]C)=O)[CH:5]=1.[CH2:18]([CH2:20][NH2:21])[OH:19]>CO>[OH:19][CH2:18][CH2:20][NH:21][C:7]([C:6]1[CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:4]([C:3]([NH:21][CH2:20][CH2:18][OH:19])=[O:17])[CH:5]=1)=[O:9]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 83316Dimethyl 5-nitroisophthalate

Product 1

HCID 13140678N~1~,N~3~-Bis(2-hydroxyethyl)-5-nitrobenzene-1,3-dicarboxamideYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing dimethyl-5-nitroisophthalate (23.9 g, 100 mmol) and ethanolamine (13.4 g, 220 mmol) in methanol (300 mL) was refluxed for 48 hours. The solvent was removed by evaporation under reduced pressure. The crude product was purified by crystallization from EtOAC:MeOH 1 ml v/v) to afford 20.0 g of pure N,N′-bis(2-hydroxyethyl)-5-nitro-1,3-benzenedicarboxamide as white crystals. m.p.=151.3-151.4° C., uncorrected

Workup

  1. temperaturewas refluxed for 48 hours
  2. customThe solvent was removed by evaporation under reduced pressure
  3. customThe crude product was purified by crystallization from EtOAC

Sources & evidence

ORD record
ord-36b3b88a204247fab995525c4112583e
Source dataset
uspto-grants-2008_04
Patent number
US07351389B2

Reaction notes

Loading…