Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 3-Methyl-1H-1,2,4-triazole, in my other articles.
Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 7170-01-6
Example 4 Synthesis of SC11 To a stirred solution of benzoic acid (116 mg, 0.94 mmol) in DCM (3 mL) were added compound 7 (200 mg, 0.94 mmol), TEA (0.4 mL, 2.82 mmol) and HBTU (536 mg, 1.39 mmol). The resulting mixture was stirred at r.t. overnight before quenched with sat. NaHCO3. The layers were separated and the aqueous layer was extracted with DCM (10 mL*3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 0?50% ethyl acetate in petroleum ether with 0.5% TEA) to provide compound 8 (164 mg, 55%) as a yellow solid. Compound 9 (303 mg, 100%) was obtained as a yellow oil by treating compound 8 (345 mg, 1.09 mmol) with 4N HCl/Dioxane (3 mL). 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 100 C. 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*20 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*35 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 14 (0.8 g, 40%) as light-yellow solid At 143 C., to molten 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*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 sat. NaHCO3 and extracted with DCM (10 mL*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. Compound 21 (55 mg, 0.18 mmol) in DMF and compound 9 (59 mg, 0.27 mmol) were added to DIPEA (0.28 mL, 1.63 mmol) and DEPBT (325 mg, 1.09 mmol). After stirring at r.t. overnight, the reaction mixture was concentrated to remove DMF under the reduced pressure. The residue was partitioned between with EA (10 mL) and sat. NaHCO3 (10 mL). The layers were separated and the aqueous layer was extracted with EA (10 mL*2). The combined organic layers was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC to give compound SC11 (22 mg, 24%).
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 3-Methyl-1H-1,2,4-triazole, in my other articles.
Reference:
Patent; Drexel University; Cocklin, Simon; (79 pag.)US2016/214998; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics