7170-01-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.
To a solution of compound 12 (0.8 g; 4.5 mmol) in N-methylpyrrolidone (5 ml), water (0.5 ml) and hydrochloric acid (5-6 drops) were added. The mixture was stirred at 100C for 6 h. The mixture was cooled to room temperature and water (100 ml) was added. Then NaHCO3 sat. (20 ml) was added, the product was extracted with EtOAc (5¡Á20 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 13 (0.6 g, 81%) as pink solid. A solution of compound 13 (1.8 g; 11 mmol) in POCl3 (20 ml) was stirred at 100 C for 12 h. Then POCl3 was evaporated under reduced pressure. To a residue ice water (100 ml) and then NaHCO3 sat. (25 ml) were added, the product was extracted with EtOAc (3¡Á35 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 14 (0.8 g, 40%) as light-yellow solid At 143C, to a melt 3-methyl-1H-1,2,4-triazole (744 mg, 8.95 mmol) under N2 atmosphere was added compound 14 (392 mg, 1.79 mmol). After stirring for 20 hrs, the reaction mixture was cooled down to r.t. and partitioned between H2O (20 mL) and EA (20 mL). The layers were separated and the aqueous layer was extracted with EA (20 mL x 3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by prep. HPLC (C18, 10% to 89% acetonitrile in water (0.1% formic acid)) to compound 19 (182 mg, 44 %) as a white solid. To a stirred solution of AlCl3 (1.588 g, 11.9 mmol) in DCM (10 mL) was added methyl 2-chloro-2-oxoacetate (389 mg, 3.18 mmol) and the resulting mixture was stirred at r.t. until it became a clear solution before introduction of compound 19 (182 mg, 0.79 mmol, in 1 mL DCM). The stirring was continued at r.t. overnight. After completion of the reaction, the mixture was quenched with saturated NaHCO3 and extracted with DCM (10 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica gel, 0 ~ 90% ethyl acetate in petroleum ether) to provide compound 20 (58 mg, 23 %) as a yellow oil. To a stirred solution of compound 20 (58 mg, 0.18 mmol) in MeOH/H2O (1 mL/2 mL) was added NaOH (15 mg, 0.37 mmol). After stirring at r.t. for 15 min, the reaction mixture was neutralized with 1N HCl, concentrated and lyophilized to provide compound 21 (73 mg, 95 %, mixed with NaCl) as a green solid.
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Reference:
Article; Tuyishime, Marina; Danish, Matt; Princiotto, Amy; Mankowski, Marie K.; Lawrence, Rae; Lombart, Henry-Georges; Esikov, Kirill; Berniac, Joel; Liang, Kuang; Ji, Jingjing; Ptak, Roger G.; Madani, Navid; Cocklin, Simon; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5439 – 5445;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics