Réaction #640530

ord-5b55b11db96547dc8fe5cd334595eae2

Équation de réaction

CC(=O)Nc1ccc(C(=O)Cn2c(-c3nonc3NCCC#N)nc3ccccc32)cc1
4-[1-(4-acetaminophenacyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(2-cyanoethyl)-amine
O=C([O-])O.[Na+]
sodium bicarbonate
Nc1ccc(C(=O)Cn2c(-c3nonc3NCCC(=O)O)nc3ccccc32)cc1
title compound
Nc1ccc(C(=O)Cn2c(-c3nonc3NCCC(=O)O)nc3ccccc32)cc1
4-[1-(4-Aminophenacyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(2-carboxyethyl)-amine

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureat reflux for two hours
  2. 2
    ExtractionExtraction with ethyl acetate
  3. 3
    Séchagedrying over sodium sulphate
  4. 4
    Filtrationfiltering
  5. 5
    Autreevaporation of the resulting filtrate to dryness

Mode opératoire

A solution of 4-[1-(4-acetaminophenacyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(2-cyanoethyl)-amine (0.061 g) in aqueous hydrochloric acid (5 ml, HCl conc.) is heated at reflux for two hours. The mixture is diluted with water and neutralized by addition of sodium bicarbonate. Extraction with ethyl acetate, drying over sodium sulphate, filtering and evaporation of the resulting filtrate to dryness gives the title compound in pure form, m.p. 174-177° C. 1H-NMR (400 MHz, d6-DMSO): 12.40 (s, 1H); 7.84 (m, 4H); 7.38 (m, 3H); 6.65 (m, 2H); 6.28 (S, 2H); 6.17 (s, 2H); 3.57 (m, 2H); 2.66 (t, 2H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE042890E1uspto-grants-2011_11