623-03-0

14401-51-5

The general procedure for the synthesis of 4-chlorobenzamidine hydrochloride from p-chlorobenzonitrile was as follows: a THF solution of 1 M LiHMDS (22 mmol) was added to a dry 50 mL reaction flask, followed by the addition of a 2 mL THF solution of p-chlorobenzonitrile (2.76 g, 20.0 mmol). The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, 5-6N HCl (in isopropanol, 15 mL) was added. The crude reaction mixture was placed at 0°C overnight. The precipitated product was collected by filtration and washed with ether to give 3.5 g (93% yield) of 4-chlorobenzamidine hydrochloride as a white solid with a melting point of 205 °C (literature value: 243-245 °C) (E. Ragona, D. L. Nelson, M. Mares-Guis, J. Amer. Chem. Soc. EPO 1975,97,. 6844-6848). - IR (KBr): ν = 3239, 3054, 1678, 1460, 1401, 1036, 715 cm-1. - 1H NMR (250 MHz, [D6] DMSO): δ = 7.60-7.77 (m, 2H), 7.85-7.97 (m, 2H), 8.4 (br.s, 3H, NH). - 13C NMR (62.9 MHz, [D6] DMSO): δ = 126.79 (Cquat), 129.36 (+), 130.57 (+), 139.1 (Cquat), 165.1 (NCN).