With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7181-87-5,1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide,as a common compound, the synthetic route is as follows.
50 mL round bottom flask that was capped with a rubber septum and containing a needle for ventilation and a glass pipette for addition of gaseous carbon dioxide, was charged with a clear colorless solution of 1,3-dimethylbenzimidazolium iodide (1b) (274.1 mg, 1 mmol) in deionized water (7 mL) (pH=6). Carbon dioxide was bubbled for 1 min followed by addition of hydrogen peroxide (65 muL (30% w/v), 0.75 mmol in 0.5 mL water, 1.5 equiv). Vigorous CO2 bubbling was maintained for 1 h under stirring during which time the solution turned yellow and then brown until the formation of a purple precipitate was detected. The mixture was filtered and washed with water (3¡Á2 mL) resulting in a clear colorless filtrate solution (pH=8). Water was removed by flushing air overnight over the surface of the solution then it was dried under high vacuum for 2 h to give a white solid. The residual solid was triturated and sonicated in acetone (3¡Á2 mL), which was then decanted off. Subsequent drying under vacuum afforded the desired product as a white powder (123 mg, 59% yield) Mp: 137-138 C. (dec.). (0410) 1H NMR (400 MHz, CD3OD): delta 7.96 (dd, J=6.2, 3.1 Hz, 2H, Ar-H), 7.74 (dd, J=6.3, 3.1 Hz, 2H, Ar-H), 4.15 (s, 6H, CH3). The N2CH and HCO3 protons could not be observed due to their rapid exchange with the deuterated solvent on the NMR time scale. 13C (1H) NMR (100 MHz, CD3OD): delta 161.38 (s, HCO3-), 143.94 (s, N2CH), 133.54 (s, Cq), 128.18 (s, CAr), 114.15 (s, CAr), 33.65 (s, CH3). (0411) ATR-IR: strong peaks for CO2 asym. str. at 1626 cm-1 and sym. str. at 1367 cm-1. (0412) Anal. Calc. for C10H12N2O3: C, 57.68; H, 5.81; N, 13.45. Found: C, 57.72; H, 5.75; N, 13.03. HRESI-MS (m/z) for C9H11N2+ [M-HCO3]+: 147.0913, Calc.: 147.0917.
The synthetic route of 7181-87-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Queen’s University at Kingston; Crudden, Cathleen M.; Horton, J. Hugh; Narouz, Mina Raafat Ryad; Unsworth, Phillip; Li, Zhijun; Nazemi, Ali; Padmos, Joseph Daniel; Eisenberger, Patrick; Zamora, Matthew Thomas; MacLean, Michael William Angus; (114 pag.)US2019/169132; (2019); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare