2-substituent-5-substituted anilino-1,3,4-oxadiazole derivatives and their synthesis method and application
An oxadiazole-based and methylaniline-based technology is applied in the directions of botanical equipment and methods, applications, and drug combinations, and can solve problems such as few therapeutic agents, unsatisfactory control effects, and pesticide residues.
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Embodiment 1
[0093] Example 1: Preparation of 2-(methylthio)-5-anilino-1,3,4-oxadiazole (TM1)
[0094] (1) Preparation of ethyl anilinate intermediate:
[0095] Throw aniline (20 g, 0.21 mol), pyridine (17 g, 0.21 mol) and anhydrous dichloromethane (100 mL) into a 250 mL three-necked flask, and slowly add ethyl chloroformate (30 g, 0.27 mol) dropwise under ice cooling Afterwards, the reaction at room temperature was completed for 2 h. The reaction was quenched, washed with water, and desolvated under reduced pressure to obtain 35.1 g of ethyl anilinate with a yield of 86%.
[0096] (2) Preparation of anilinoformohydrazide intermediate
[0097] Throw ethyl anilinate (16 g, 0.18 mol) and 80% hydrazine hydrate (90 g, 1.80 mol) into a 100 mL three-necked round-bottomed flask, and heat up to reflux for 20 h to complete the reaction. After cooling, white crystals were precipitated, which were obtained by suction filtration to obtain anilinoformohydrazide, and recrystallized in absolute ethano...
Embodiment 2
[0103] Example 2: Preparation of 2-(4-methylbenzylthio)-5-anilino-1,3,4-oxadiazole (TM2)
[0104] Steps (1)-(4) are the same as in Embodiment 1.
[0105] (5) Add intermediate 2-mercapto-5-(anilino)-1,3,4-oxadiazole potassium salt (0.50g, 2.0 mmol), 15 mL water, potassium carbonate (0.28 g, 2.0 mmol), stirred, added (0.34 g, 2.5 mmol) iodomethane and KI (16.6 mg, 0.10 mmol). The reaction was stirred at room temperature (20 °C) for 5 h. The reaction solution was extracted with dichloromethane, concentrated, and separated by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a white solid: 0.224 g, yield 35.5%.
Embodiment 3
[0106] Example 3: Preparation of 2-(4-fluorobenzylthio)-5-(2-methylanilino)-1,3,4-oxadiazole (TM3)
[0107] Steps (1)-(4) are the same as in Embodiment 1.
[0108] (5) Add intermediate 2-mercapto-5-(2-methylanilino)-1,3,4-oxadiazole potassium salt (0.80 g, 3.3 mmol), 15 mL water, Potassium carbonate (0.45 g, 3.3 mmol), stirred, added (0.77 g, 4.1 mmol) 4-fluorobenzyl bromide and KI (27.1 mg, 0.16 mmol). The reaction was stirred at room temperature (20 °C) for 5 h. The reaction solution was extracted with dichloromethane, concentrated, and separated by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a white solid: 0.416 g, yield 40.4%.
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