Thiazolyl acrylonitrile compound and its application
A technology of thiazolyl acrylonitrile and compound, which is applied in thiazolyl acrylonitrile compound and its application field, can solve the problems that insecticidal and acaricidal activities have not been disclosed, and achieve high aphidicidal activity and high insecticidal effect
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Embodiment 1
[0065] Embodiment 1, the preparation of compound 8,9
[0066] (1) Preparation of 4-(chloromethyl)-2-phenylthiazole
[0067]
[0068] 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- Phenylthiazole, yellow oil, yield: 69%.
[0069] (2) Preparation of 2-(2-phenylthiazol-3-yl)acetonitrile
[0070]
[0071] A...
Embodiment 2
[0081] Embodiment 2, the preparation of compound 38
[0082] (1) Preparation of 3-(2-bromo-4-methylthiazol-5-yl)-3-hydroxyl-2-(2-phenylthiazol-4-yl)acrylonitrile
[0083]
[0084] Under an ice-water bath, add 2-(1-phenylthiazol-4-yl)acetonitrile (1.00 g, 0.005 mol), (2-bromo-4-methylthiazol-5-yl) (1H-pyridine Azol-1-yl)methanone (1.36 g, 0.005 mol), 20 ml of tetrahydrofuran, stirred for about 1 hour, and potassium tert-butoxide (1.12 g, 0.010 mol) was added in batches. 6 hours. The reaction solution was poured into 150 ml of water, extracted with 100 ml of ethyl acetate, the resulting aqueous phase was adjusted to pH 2~3 with concentrated hydrochloric acid, extracted with 3×100 ml of ethyl acetate, and the organic phase was washed with saturated aqueous sodium bicarbonate (100 ml), washed with saturated aqueous sodium chloride solution (100 ml), dried over anhydrous magnesium sulfate, and concentrated to give 1.27 g of 3-(2-bromo-4-methylthiazol-5-yl)-3-hydroxy -2-(2-Phe...
Embodiment 3
[0088] Embodiment 3, the preparation of compound 58
[0089]
[0090] Under ice-water bath, add 3-(2-bromo-4-methylthiazol-5-yl)-3-hydroxyl-2-(2-phenylthiazol-4-yl)acrylonitrile (0.40 g , 0.001 mol), 10 ml of acetonitrile, triethylamine (0.10 g, 0.001 mol), and then dropwise added ethyl chloroformate (0.11 g, 0.001 mol) into the reaction flask, after the addition was completed, the temperature was raised to room temperature and the reaction 2 hour, the reaction solution was poured into 50 ml of water, extracted with ethyl acetate 3×100 ml, the organic phase was washed with saturated aqueous sodium bicarbonate (100 ml), saturated aqueous sodium chloride (100 ml), and washed with anhydrous sulfuric acid After drying over magnesium and concentrating under reduced pressure, the residue was separated by column chromatography (eluent: ethyl acetate:petroleum ether=1:20) to obtain compound 58 as a mixture of stereoisomers (E:Z=2:5 ), 0.29 g of yellow oil, yield 60%.
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