16681-65-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16681-65-5 as follows.
Intermediate 77: step a N-methoxy-N-1-dimethyl-1H-1,2,3-triazole-5-carboxamide A solution of 1 -methyl- 1H- 1 ,2,3-triazole (12.9 g, 155 mmol) in THF (260 mL) was cooled to – 45 C. Maintaining a temperature of < -35 C, -BuLi (62.5 mL, 2,5 M in hexanes, 155 mmol) was added over 10 minutes. The reaction mixture was stirred for 30 minutes with cooling to -45 C and then treated with a sub-surface stream of CQ2(g)for a period of 2 hours. After flushing the -35 C slurry with Ng)for 5 minutes, thionyi chloride (11 ,8 mL, 163 mmol) was added. The mixture was allowed to warm to room temperature with stirring over 1.25 hours. Then, N,0-dimethyihydroxylamine hydrochloride (18.14 g, 186 mmol) and AyV-diisopropy ethylamine (68.3 mL, 396 mmol) were added and the resulting mixture stirred for 15 hours. Aqueous sodium carbonate (500 mL, 10 wt%) was then added, and the layers were mixed and separated. The aqueous layer was washed with dichloro methane (250 mL and then 125 mL), and the combined organic layers were dried over MgS04, filtered, and concentrated. The residue was taken up in ethyl acetate (225 mL), treated with MgS04, and filtered through a pad of silica gel (115 g). The silica gel pad was washed with additional ethyl acetate (800 mL). The eluent was concentrated to provide the title compound as a yellow solid
According to the analysis of related databases, 1-Methyl-1H-1,2,3-triazole, the application of this compound in the production field has become more and more popular.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics