Synthesis
General procedure for the synthesis of 4-methoxybenzenecarbamidine hydrochloride from 4-methoxybenzyl cyanide: 4-methoxybenzyl cyanide (2.1 g, 15.7 mmol) was mixed with sodium methanolate (86 mg, 1.57 mmol) in 20 mL of anhydrous methanol, and the reaction was stirred for 48 hours at room temperature. Subsequently, ammonium chloride (0.84 g, 15.7 mmol) was added to the reaction system and stirring was continued for 24 hours. After completion of the reaction, the precipitate was collected by filtration, washed with ether and dried under vacuum to afford the target product 4-methoxybenzenecarboximidamide hydrochloride (1.3 g, 44.5% yield). Mass spectrum (ESI) m/z: 151.1 ([M+H]+).
References
[1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 783 - 795
[2] Journal of the American Chemical Society, 1985, vol. 107, # 9, p. 2743 - 2748
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 3, p. 613 - 623
[4] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 4, p. 933 - 940
[5] Patent: US6218538, 2001, B1
