Synthetic Route of 16681-65-5, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
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
Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1-Methyl-1H-1,2,3-triazole.
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