Reaktion #444771

Reaktionsgleichung

hydrochloric acid

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

1,2-diamino-4-phenyl-imidazole

→

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

Lösungsmittel

isopropanol

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONDuring that time, the starting materials dissolve
2. 2
   Sonstigethe title compound gradually crystallizes out
3. 3
   TemperaturAt the end of the reaction time, the mixture is cooled
4. 4
   SonstigeThe product that has crystallized out
5. 5
   Filtrationis filtered off with suction
6. 6
   Waschenwashed with isopropanol
7. 7
   Sonstigedried

Vorschrift

6 ml of 32% hydrochloric acid (Merck, Darmstadt, Germany; p.a.) are added, with stirring, to a mixture of 4.1 g (0.02 mol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 3.5 g (0.02 mol) of 1,2-diamino-4-phenyl-imidazole (see Beyer H. et al., Chem. Ber. 101, 3151 (1968)) and 150 ml of isopropanol, and the mixture is stirred at 80° C. for 5 hours. During that time, the starting materials dissolve and the title compound gradually crystallizes out. At the end of the reaction time, the mixture is cooled. The product that has crystallized out is filtered off with suction, washed with isopropanol and dried. The product crystallizes with one mole of isopropanol, m.p. 238°-240° C., 1H-NMR (DMSO/D2O): δ=8.24 (d, 1H); 7.88 (s, 1H); 7.73 (d, 1H); 7.55-7.68 (m, 3H); 7.34-7.5 (m, 3H); 3.26 (s, 4H).

Quelle