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. 288-88-0, name is 1H-1,2,4-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1H-1,2,4-Triazole
Example 2 Synthesis of 2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-difluorophenyl)-1,3-dioxolane-4-thiol Sodium triazole was prepared in-situ by azeotropically distilling a mixture of 1,2,4-triazole (0.5 mol), sodium hydroxide solution (50%, 35.2 mL), toluene, (250 mL) and dimethylsulfoxide (250 mL) to a Karl Fisher water content less than 0.4% (by a Karl Fisher titration). The solution was cooled to 25 C., then a anhydrous toluene solution of 2-(bromomethyl)-2-(2,4-difluorophenyl)-4-(ethylthio)-1,3-dioxolane (Chemical Structure 8, 1.8 mol) was added. The temperature was increased to 75 C. and held at that temperature to reaction completion (monitored by TLC). Then the reaction mixture was cooled to 35 C. and quenched with dilute sodium hydroxide aqueous solution slowly to keep the temperature below 45 C. After the resulting mixture was cooled to 25 to 35 C., water and toluene were added. After the phases were separated, the aqueous phase was washed with toluene 3 to 5 times. The combined organic phases were concentrated under a maximum temperature of 70 C. The ethyl group of the thioester (1 mol) was removed by treated the resulting residue with sodium methoxide (approximately 8 mol) in dimtheylformamide (300 mL). The reaction mixture was stirred under nitrogen over night at 120 C. After cooling to room temperature, the reaction was quenched by adding methyl iodide (5 mol) under constantly stirring. Then the mixture was poured into water (350 mL) and extracted with tert-butyl methyl ether (100 mL*3). The organic phase was washed with saturated sodium sulphate solution and condensed. The residue was dissolved in warm toluene and washed with dilute hydrochloric acid aqueous solution, up to two times. After filtration of the precipitate and crystallization from isopropanol/Isopropyl ether (8/2, v/v), the D form of Chemical Structure A where X is -SH was obtained in ~65% yield (Chemical Structure 9).
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Reference:
Patent; Wu, Nian; Keller, Brian Charles; US2010/143455; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics