Réaction #674283

ord-00d1f0ebe0fa4bef90831e3d948b2145

Équation de réaction

OO
hydrogen peroxide
CCN(c1ccc(N)cc1)C(C)C.Cl
N-ethyl-N-isopropyl-4-aminoaniline hydrochloride
CCCCOc1ccc(N)cc1N.Cl.Cl
4-butoxybenzene-1,3-diamine dihydrochloride
CCO
ethanol
N
ammonia
CCCCOC1=CC(=Nc2ccc(N(CCO)CCO)cc2)C(N)=CC1=N
2-[[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)phenyl](2-hydroxyethyl)amino]ethanol

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe ethanol is removed
  2. 2
    Autrethe coupling product formed
  3. 3
    Extractionis extracted with butanol
  4. 4
    AutreAfter removal of the butanol under vacuum

Mode opératoire

To a solution of 0.925 g (0.003 mol) of N-ethyl-N-isopropyl-4-aminoaniline hydrochloride and 0.76 g (0.003 mol) of 4-butoxybenzene-1,3-diamine dihydrochloride in 2 ml of water and 6 ml of ethanol, brought to pH 9.5 with 20% aqueous ammonia, are added 10.2 ml of 6% aqueous hydrogen peroxide solution. After stirring for 24 hours at room temperature, the ethanol is removed and the coupling product formed is extracted with butanol. After removal of the butanol under vacuum, the gummy residue is taken up in ethyl acetate and then in ether. 0.470 g of 2-[[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)phenyl](2-hydroxyethyl)amino]ethanol 10 is obtained in the form of a blue-black powder after drying.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09226883B2uspto-grants-2016_01