Synthesis
Methanol (500 mL) was cooled to -20 °C and SOCl2 (36 mL, 0.5 mol) was added slowly and dropwise under vigorous stirring while controlling the temperature of the reaction mixture below -10 °C. Subsequently, iminodiacetic acid (13.3 g, 0.1 mol) was added all at once. The reaction mixture was stirred continuously at room temperature for 24 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure at room temperature and the residue was crystallized with methanol. The product aminobisacetic acid dimethyl hydrochloride 16 g (81% yield) was obtained as a white crystalline solid. The product was characterized as follows: 1H NMR (300 MHz, D2O) δ=4.13 (s, 4H), 3.85 (s, 6H); 13C NMR (75 MHz, D2O) δ=168.08, 54.12, 47.66. Elemental analysis results (C6H12ClNO4): calculated values C 36.47%, H 6.12%, N 7.09%; measured values C 36.52%, H 6.01%, N 6.98%.
References
[1] Organic Preparations and Procedures International, 2002, vol. 34, # 1, p. 87 - 94
[2] Heterocycles, 2008, vol. 76, # 2, p. 1237 - 1248
[3] Molecules, 2008, vol. 13, # 5, p. 1111 - 1119
[4] Synthesis (Germany), 2016, vol. 48, # 24, p. 4580 - 4588
[5] Inorganic Chemistry, 2018, vol. 57, # 15, p. 8964 - 8977
