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

HRID 1814222Notes

Reaction equation

HRID 1814222 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.

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-3816b5a900d34d37a4d848223ddab355
Source dataset
uspto-grants-2005_04
Patent number
US06875864B2

Reaction notes

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