Reaktion #444798

Reaktionsgleichung

hydrochloric acid

4-(N-hydroxyarnidino)-2,3-dihydro-1H-inden-1-one oxime

1,2-diamino-4-(2-naphthyl)-imidazole

→

title compound

1-[4-(N-Hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(2-naphthyl)-imidazole dihydrochloride

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled to 20° C.
2. 2
   Filtrationfiltered
3. 3
   Waschenwashed with isopropanol
4. 4
   workup.STIRRINGThe suspension is stirred at room temperature for 15 hours
5. 5
   Filtrationis then filtered
6. 6
   Waschenthe crystallizate is washed with methylene chloride

Vorschrift

7 ml of concentrated hydrochloric acid are added, with stirring, to a mixture of 2.01 g (9.8 mmol) of 4-(N-hydroxyarnidino)-2,3-dihydro-1H-inden-1-one oxime, 2.2 g (9.8 mmol) of 1,2-diamino-4-(2-naphthyl)-imidazole (see J. Heterocycl. Chem. 11, 327-329 (1974)) and 25 ml of isopropanol, and the mixture is stirred at 120° C. for 24 hours. The mixture is cooled to 20° C., filtered and washed with isopropanol, and the filtration product is taken up in 60 ml of methylene chloride. The suspension is stirred at room temperature for 15 hours and is then filtered, and the crystallizate is washed with methylene chloride. In that manner there is obtained the title compound, m.p. 265°-270° C., 1H-NMR (DMSO/D2O): δ=8.32 (s, 1H); 8.29 (d, 1H); 8.19 (s, 1H); 8.04 (d, 1H); 7.88-7.98 (m, 3H); 7.81 (d, 1H); 7.53-7.68 (m, 3H); 3.38 (s, 4H).

Quelle