4-(4-chlorophenyl)-1H-imidazole-1,2-diamine → HCID 178478842, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.026 g (5 mmol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 1.043 g (5 mmol) of 1,2-diamino-4-(4-chlorophenyl)-imidazole (see Beyer H. et al., Chem. Ber. 101, 3151 (1968)) and 20 ml of 4N hydrochloric acid is heated at 120° C. for 18 hours, with stirring, and is then concentrated by evaporation in vacuo. 25 ml of ethanol are added to the crystalline residue, the mixture is cooled to 5° C., with stirring, and is filtered, and the crystallizate is washed with a small amount of ethanol and diethyl ether. The crude title compound, dried under a high vacuum, contains 8.17% water and melts at 226°-228° C. (decomp.), 1H-NMR (D2O): δ=8.06 (d, 1H); 7.75 (d, 1H); 7.55 (t, 1H); 7.40 (s, 1H); 7.38 (d, 2H); 7.28 (d, 2H); 3.21-3.27 (m, 2H), 3.03-3.09 (m, 2H).

Provenance & Evidence