Reference of 16681-65-5, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, its 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.
7.1 : 1 -Methyl-1 H-[1 ,2,3]triazole (1 .50 g; 17.150 mmol) was dissolved in dry THF (30.0 mL) under argon and cooled to -65 C. Butyllithium (2.5 M in hexane; 6.86 mL; 17.150 mmol) was added dropwise over a period of 10 min. The temperature was hold between -65 C and -60 C. A colorless suspension was formed, which was stirred at – 65 C for 1 h. 1 -Methyl-1 H- pyrazole-4-carbaldehyde (1 .89 g; 17.150 mmol), dissolved in dry THF (10.0 mL), was added dropwise at -65 C and the mixture stirred at – 65 C for 15 min. The reaction mixture was slowly warmed to 0 C within 1 .5 h and then quenched with methanol (10 ml_) and evaporated to dryness. The crude residue was dissolved in dry THF (50.0 ml_) and water (15.0 ml_). (0380) Manganese(IV) oxide (2.98 g; 34.299 mmol) was added, and the mixture was stirred at 80 C overnight. Manganese(IV) oxide (2.98 g; 34.299 mmol) was added and the mixture was stirred for further 24 h at 80 C. The mixture was filtered over kieselguhr. The residue was washed with dichloro- methane/methanol(30%). The combined filtrates were evaporated to an aqueous residue. A precipitate was formed, which was filtered by suction and washed with little water, acetonitrile and MTBE and dried under vacuum at 50 C for 1 h. The filtrate was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with sodium sulfate, filtered by suction and evaporated to dryness. The solid residue was triturated with little acetonitrile, filtered by suction and washed with little acetonitrile and MTBE, and dried under vacuum at 50 C for 1 h. Yield: 2.38 g colorless solid; (0381) LC/MS, Rt: 1 .29 min; (M+H) 192.2
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Reference:
Patent; MERCK PATENT GMBH; BUCHSTALLER, Hans-Peter; (101 pag.)WO2018/87021; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics