Synthetic Route of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: A mixture of 1-methyl-1H-imidazole-2-carboxylic acid (0.130 g,1mmol), EDC.HCl (0.29 g, 1.5mM), HOBt (0.20 g, 1.5mmol) and Et3N(0.15 g, 1.5 mM) in dichloromethane (10 mL) was stirred for 1 h at 0 C. Then, L-phenylalanine methyl ester.HCl (1.05 mM) was added into the solution. The reaction mixture was stirred for 12 h at 25 Cand then evaporated to dryness. The ester obtained was washed with water and extracted with dichloromethane (Scheme 1). To a solutionof the ester (1 equiv) in a dichloromethane/methanol (9:1 v/v)mixture, was added a methanolic solution of NaOH (3 equiv) withfinal concentration of the alkali being about 0.1-0.2 N. The reaction was monitored by TLC for the disappearance of starting ester. After the completion of the reaction, the solvents were removed under vacuum and the residue was diluted with water. Then, the aqueous phase was acidified to pH 2-3 with dilute HCl and extracted with ethyl acetate. The combined organic layers were dried with anhydrous sodium sulfate (Na2SO4) and the solvent was removed to afford the acid (PAIC). Single crystal of PAIC was isolated by slow evaporation of the solvent. Yield: 143 mg (74%), M.P- 129 C; Anal.Calc. for C14H15N3O3: C, 61.53; H, 5.53; N, 15.38. Found C, 61.13; H,5.45; N,15.18; 1H NMR (DMSO-d6, 400MHz): delta/ppm3.16 (d, J 4Hz,2H, CH2), 3.8 (s, 3H, NeCH3), 4.6 (m, H, chiral H), 6.9e7.2 (m, 7H,Aromatic H), 8.2 (d, J 8.4 Hz, 1H, amide-NH); 13C NMR: 34.9 (CH3),36.2 (eCH2), 52.9 (CeNH), 158.5 (COeN), 172(eCOO); FT-IR (KBr, cm-1)1555 (NeH), 1602 (eC]N), 3292 (HOeCO), 1673 (C]Oamide), 2931 (CeH); ESI mass: m/z 272.9.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.
Reference:
Article; Annaraj; Mitu; Neelakantan; Journal of Molecular Structure; vol. 1104; (2016); p. 1 – 6;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem