تفاعل #444792

معادلة التفاعل

p-toluenesulfonate

hydrochloric acid

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

1,2-diamino-4,5-dihydro-imidazole hydrochloride

styrene/divinylbenzene

→

title compound

1-[4-(N-Hydroxyamidino)-2,3-dihydro- 1H-inden-1-ylideneamino]-2-amino-4,5-dihydro-imidazole dihydrochloride

المذيبات

isopropanol

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction mixture is filtered while hot and the filtration product
2. 2
   غسيلis washed with isopropanol
3. 3
   أخرىrecrystallized from hot water

الإجراء التجريبي

0.5 ml of 32% hydrochloric acid (Merck, Darmstadt, Germany; p.a.) is added, with stirring, to a mixture of 0.51 g (0.0025 mol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 0.342 g (0.0025 mol) of 1,2-diamino-4,5-dihydro-imidazole hydrochloride [m.p. 245°-246° C.; prepared from the corresponding p-toluenesulfonate salt, see EP 0 327 919, Example 12, by ion exchange on ®Amberlite IRA-400 (anion exchanger based on a styrene/divinylbenzene polymer with quaternary ammonium groups in the Cl- form; Fluka, Buchs, Switzerland)] and 12 ml of isopropanol, and the reaction mixture is stirred at 80°-90° C. for 16 hours. The reaction mixture is filtered while hot and the filtration product is washed with isopropanol and recrystallized from hot water. In that manner there is obtained the title compound, m.p. >245° C., 1H-NMR (D2O): δ=8.08 (d, 1H); 7.72 (d, 1H); 7.56 (t, 1H); 4.14 (t, 2H); 3.81 (t, 2H); 3.3 (m, 2H); 3.15 (m, 2H).

المصدر