Electric Literature of 288-88-0, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 288-88-0, name is 1H-1,2,4-Triazole, molecular formula is C2H3N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
Example 8; In DMSO (26.4ml), (2R, 3R)-3-(2,4-difluorophenyl)-3,4-epoxy-2-butanol (20.0g, 0.1 mol) and 1,2,4-triazole (10.4g, 0.15 mol) were dissolved and heated to about 60C with stirring. 20% aqueous sodium hydroxide solution (6.0g, 0.03 mol) was dropped thereto over about 15 minutes and further stirred for 5 hours at the same temperature for the reaction. After the reaction, the mixture was cooled, diluted with water (40ml) and neutralized (pH 6-7) with 35% hydrochloric acid. Ethyl acetate (100ml) was added, stirred and subjected to phase separation. The water layer was extracted with ethyl acetate (100ml) three times. A part of the ethyl acetate was taken and concentrated, and then NMR was measured to confirm the sample is (2R, 3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol. 1H-NMR (CDCl3, delta ppm) 0.98 (3H, d, J=6Hz), 2.62 (1H, d, J=9Hz), 4.31-4.34 (1H, m), 4.79, 4.80 (each 1H, d, J=14Hz), 4.82 (1H, s), 6.72-6.79 (2H, m), 7.38-7.45 (1H, m), 7.83, 7.85 (each 1H, s) The ethyl acetate layers were combined and then distilled off under a reduced pressure. Subsequently, toluene (50ml) and triethylamine (65.8g, 0.65 mol) were added thereto and cooled to about 5C and stirred. Methanesulfonyl chloride (17.2g, 0.15 mol) was dropped thereto over about one hour and stirred for 30 minutes at the same temperature for the reaction. After the reaction, water (50 ml) was poured into and stirred, and then water layer was separated and extracted with toluene (100ml) three times. The combined toluene layers were washed with water and the solvent was distilled off under a reduced pressure. The concentrated residue was subjected to recrystallization from a mixed solvent of toluene/heptane (20/80; v/v, 400ml) to give (2R, 3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane. (11.6g, yield 46.2%, optical purity (HPLC condition-1) 100%e.e., mp 89C)
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Reference:
Patent; Sumitomo Chemical Company, Limited; EP1818332; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics