O-trifluoromethylphenyl acrylonitrile compound and application thereof
A technology of trifluoromethylphenylacrylonitrile and compounds, which is applied in the field of o-trifluoromethylphenylacrylonitrile compounds, and can solve the problems that insecticidal and acaricidal activities have not been disclosed.
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Embodiment 1
[0113] Embodiment 1, the preparation of compound 16,17
[0114] (1) Synthesis of 4-chloromethyl-2-phenylthiazole
[0115]
[0116] Add thiobenzamide (20.00 g, 0.146 mol), 200 ml of methanol, and 1,3-dichloroacetone (22.21 g, 0.157 mol) into the three-necked flask, raise the temperature to reflux, and react under reflux for 3 hours. After the reaction, the temperature was lowered to below 30°C, the reaction solution was poured into 50 ml of water, extracted with 3×50 ml of ethyl acetate, and the organic phase was washed with saturated aqueous sodium bicarbonate (50 ml), saturated aqueous sodium chloride (50 ml) After washing, drying with anhydrous magnesium sulfate, and concentration under reduced pressure, the residue was separated by column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain 21.00 g of 4-chloromethyl-2-phenyl Thiazole, yellow oil, yield 69%.
[0117] (2) Synthesis of 4-cyanomethyl-2-phenylthiazole
[0118]
[0119] Add sodium cya...
Embodiment 2
[0129] Embodiment 2, the preparation of compound 469
[0130] (1) Synthesis of 4-chloromethyl-2-(2,6-difluorophenyl)oxazole
[0131]
[0132] Add 2,6-difluorobenzamide (10.00 g, 0.064 mol) and 1,3-dichloroacetone (16.20 g, 0.128 mol) to a 100 mL round bottom flask, raise the temperature to reflux and keep the reaction under reflux conditions for 4 hours. After stopping the reaction, cool to room temperature naturally, pour into 500 ml of water, extract with 3 × 100 ml of ethyl acetate, wash the organic phase with 3 × 100 ml of saturated aqueous sodium chloride solution, dry with anhydrous magnesium sulfate, and concentrate the column Chromatographic separation (eluent: ethyl acetate:petroleum ether=1:3) gave 11.50 g of 4-chloromethyl-2-(2,6-difluorophenyl)oxazole as a yellow solid with a yield of 76%.
[0133] (2) Synthesis of 2-(2,6-difluorophenyl)-4-cyanomethyloxazole
[0134]
[0135] Add 4-chloromethyl-2-(2,6-difluorophenyl) oxazole (20.00 g, 0.087 mol) into a 50 ...
Embodiment 3
[0142] Embodiment 3, the preparation of compound 575
[0143] (1) Synthesis of 3-methyl-1-phenyl-1H-pyrazole
[0144]
[0145] Add phenylhydrazine (5.00 g, 0.046 mol), 4,4-dimethoxy-2-butanone (7.30 g, 0.055 mol), and 40 ml of ethanol into the reaction flask, heat up to reflux, and reflux for 2 hours. Concentrated hydrochloric acid (0.5 ml) was added dropwise to the reaction solution, and reflux was continued for 2 hours. After the reaction was completed, the temperature was lowered to below 30°C, the reaction solution was poured into 200 ml of water, extracted with 3×150 ml of ethyl acetate, the organic phase was washed with saturated aqueous sodium chloride solution (150 ml), and dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was separated by column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain 5.00 g of 3-methyl-1-phenyl-1H-pyrazole, yellow oil, yield 68%.
[0146] (2) Synthesis of 3-bromometh...
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