Related Products of 956317-36-5, New Advances in Chemical Research in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
The amine DBT salt 16 (5,67 kg, 9.09 mol) was charged to a vessel and inerted. DCM (28 L) was added, followed by 4 N Sodium Hydroxide solution (prepared from 10 N NaOH [22,4 L] and water [36 L]), The slurry was then stirred at ambient temperature for 1 h until a solution was obtained. The layers were separated and the aqueous phase treated with sodium chloride solution (10.1 kg in 20 L water). DCM (5 L) was then added and the bi-phasic mixture stirred for 10 min before separating the layers. The combined organic layers were then concentrated under reduced pressure to a 10 L volume. The solution of the free amine was used directly in the next reaction. The triazole acid 5 (13.25 kg, 65.2 mol), DCM (88 L) and DMF (1.35 L, 17.4 mol) were charged to a vessel and the resulting suspension was cooled to 0 C. Oxalyl chloride (8.28 kg, 65,2 mol) was added portion wise keeping the internal temperature between 5 and 10 C (the anhydride formed above 10 C), then the reaction was aged for 30 min at thistemperature. HPLC analysis showed acid 5 remained; an additional charge of oxalyl chloride (160 g, 1.26 mol) was made, and the solution stirred at 5 C for 30 minutes. A solution of the amine (R)-ll (16.5 kg, 62.1 mol) and triethylamine (13.19 kg, 130.0 mol) in DCM (~8 L) was added to the acid chloride over 30 minutes, keeping the internal temperature less than 15 C, The resulting slurry was aged for 30 minutes and then quenched by the addition of water (167 L) over 10 minutes, keeping the internal temperature <15 C. The lower organic layer was removed, and then concentrated under atmospheric pressure to a volume of 100 L. Assay at this stage showed 27.3 kg 1, 98%. The solution was solvent switched to MeCN (ca. 560 L, 20 mL/g) by distillation under reduced pressure at <50 C. The MeCN solution was treated with ecosorb C-941 (2.8 kg) slurried in MeCN (10 L). The resulting slurry was aged for 30 min then filtered through a Solka Flok pad and a 0.1 um cartridge filter washing with MeCN (2 x 30 L). The MeCN filtrate was concentrated under reduced pressure at <50 C to a final volume of ca 112 L. The slurry was cooled to 25 C and water (280 L) added over 40 minutes. The resulting slurry was aged at 20 C for 1 hour, then filtered, washing the cake with 5:1 water: MeCN (60 L) followed by water (40 L). The solid was dried in the vacuum oven with nitrogen purge overnight at 50 C. The final target 1 was isolated as a white solid, 26.72 kg, 95%, 98.5% ee, 99.6 LCAP. m.p. 153.1 C.[
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics