Reaktion #53514

ord-e07988679b094e7aa963e37ef2a90aed

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OCC2CO2)cc1
glycidyl tosylate
Nc1c(O)cccc1[N+](=O)[O-]
2-amino-3-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
→
Nc1c(OCC2CO2)cccc1[N+](=O)[O-]
title compound
Nc1c(OCC2CO2)cccc1[N+](=O)[O-]
2-amino-3-nitro-1-(2,3-epoxypropoxy)benzene

Edukte

Cc1ccc(S(=O)(=O)OCC2CO2)cc1
glycidyl tosylate
Nc1c(O)cccc1[N+](=O)[O-]
2-amino-3-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe mixture is heated
  2. 2
    Temperaturat reflux for 18 hours
  3. 3
    FiltrationThe mixture is filtered
  4. 4
    Sonstigethe solvent is evaporated under reduced pressure
  5. 5
    SonstigeThe crude reaction product
  6. 6
    Sonstigeis purified by flash chromatography, elution

Vorschrift

21.7 g (0.095 mol) of glycidyl tosylate, 10 g (0.0475 mol) of 2-amino-3-nitrophenol and 6.5 g of crushed K2CO3 are mixed in acetone and the mixture is heated at reflux for 18 hours. The mixture is filtered and the solvent is evaporated under reduced pressure. The crude reaction product is purified by flash chromatography, elution being carried out with a 9/1 hexane/ethyl acetate mixture. The title compound is obtained. M.p.: 7°-78° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858629B1uspto-grants-2005_02