New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 288-36-8, name is 1H-1,2,3-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-36-8
But-3-yn-1-ol (49.57 g, 707.2 mmol) and triethylamine (107.7 mL, 777 mmol, dried over KOH) were dissolved in dry dichloromethane (500 mL) under a nitrogen atmosphere and cooled to 0 C. Methanesulfonyl chloride (54.8 mL, 708 mmol), dissolved in 500 mL of dry dichloromethane was added within 90 minutes while keeping the temperature below 5 C. The mixture was stirred for 3.5 hours at room temperature, then poured onto 2.5 L of ice water. The organic phase was separated and washed with 2×500 mL of water and 1×250 mL of brine and dried over sodium sulfate. The volatiles were removed to yield 94.18 g of the methane sulfonate (631.2 mmol, 89.2%) as a yellow liquid. A suspension of NaOH (37.86 g, 946.5 mmol), sodium iodide (94.65 g, 631.5 mmol) and 1H-[1,2,3]Triazole (61.03 g, 883.6 mmol) in 2-methyl-2-butanol (750 mL) was refluxed for 1 h under an inert atmosphere. After cooling to room temperature the methane sulfonate (94.18 g, 631.2 mmol) was added within 5 minutes. The resulting suspension was then heated to reflux for 3 hours, cooled to room temperature and concentrated on a rotary evaporator at 45 C. Water (500 mL) and dichloromethane (1 L) were added and the organic phase was separated, dried over sodium sulfate and the volatiles removed at 30 C. The residue was distilled at 1.5 mbar. A forerun was collected at 20-70 C. The main fraction distilled at 123-129 C. as a colorless, turbid liquid. After filtration over Celite (a pad of diatomite) 1-But-3-ynyl-1H-[1,2,3]triazole was obtained as a colorless liquid (29.8 g, 40%). The content according to GC/FID was >98%. -H-NMR (CDCl3) delta=2.05 (t, 1H, C?CH), 2.75 (dt, 2H, CH2-C?CH), 4.5 (t, 2H, CH2-triazole), 7.65 (s, 1H, triazole), 7.70 (s, 1H, triazole).
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Reference:
Patent; Bossenmaier, Birgit; Friebe, Walter-Gunar; Friess, Thomas; Kling, Lothar; Rueth, Matthias; Voss, Edgar; US2005/203064; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics