A kind of cyanuric chloride derivative and its preparation method and application
A technology of polycyanogen chloride derivatives and dichloride, applied in botany equipment and methods, chemicals for biological control, applications, etc., to achieve high yield, simple synthesis process, and easy industrialization
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Embodiment 1
[0024] Preparation of 2-chloro-4-(4-trifluoromethylanilino)-6-methylamino-1,3,5-triazine
[0025] The preparation of intermediate 2,6-dichloro-4-(4'-trifluoromethylanilino)-1,3,5-triazine, the reaction formula is as follows:
[0026]
[0027] Add 1.9 g (10 mmol) of cyanuric chloride to a 150 mL three-necked flask, add 30 mL of acetone, stir to dissolve, and cool to 0°C in an ice bath. Slowly add 1.6g (10mmol) of p-trifluoromethylaniline in 20ml of acetone solution dropwise, after 10min, the reaction was stirred at 0°C for 3h. After the reaction was completed, the pH value of the reaction system was adjusted to 6 with a 10% aqueous solution of sodium carbonate by mass percentage, and a white solid precipitated after standing still. After suction filtration, the filter cake was recrystallized with ethanol and water, and after drying, 2.47 g of white solid was obtained. Yield: 80%, mp: 155~157℃, 1 H NMR (DMSO, 400MHz) δ: 7.73~7.75 (d, J=8.56MHz, 2H, ArH), δ: 7.84~7.86 (d, J...
Embodiment 2
[0031] The preparation of 2,6-dichloro-4-(4'-trifluoromethylanilino)-1,3,5-triazine is the same as in Example 1;
[0032] 2-Chloro-4-(4-trifluoromethylanilino)-6-ethylamino-1,3,5-triazine
[0033]
[0034] Add 0.64g (10mmol) of ethylamine aqueous solution into a 150mL three-necked flask, add 30mL of acetone, dropwise add 0.84g (10mmol) of sodium bicarbonate aqueous solution, react for 5min, and then dropwise add the intermediate 2,6-dichloro-4- (4'-trifluoromethylanilino)-1,3,5-triazine 3.09g (10mmol) in acetone solution, react at room temperature for 4h. After the reaction was completed, it was allowed to stand, and the solvent was removed. The solid was washed with distilled water (2×15ml), recrystallized with acetone, and dried to obtain 1.71g of white solid powder. Yield: 54%, mp: 213-214°C, 1 H NMR (DMSO, 400MHz) δ: 1.1~1.2 (m, 3H, CH 3 ), δ: 3.26~3.39 (m, 2H, CH 2 ), δ: 7.5~7.6 (m, 2H, ArH), δ: 7.92~7.97 (m, 2H, ArH), δ: 8.2 (s, 1H, NHCH 2 CH 3 ), δ: 10.2~10.3 (...
Embodiment 3
[0036] The preparation of 2,6-dichloro-4-(4'-trifluoromethylanilino)-1,3,5-triazine is the same as in Example 1;
[0037] 2-Chloro-4-(4-trifluoromethylanilino)-6-n-propylamino-1,3,5-triazine
[0038]
[0039] Add 0.59g (10mmol) of n-propylamine to a 150mL three-necked flask, add 30mL of acetone, add dropwise an aqueous solution of 0.84g (10mmol) of sodium bicarbonate, react for 5min, and then add dropwise the intermediate 2,6-dichloro-4 -(4'-trifluoromethylanilino)-1,3,5-triazine 3.09g (10mmol) in acetone solution, react at room temperature for 4h. After the reaction was completed, let it stand still, remove the solvent, wash the solid with distilled water (2×15ml), recrystallize with acetone, and dry to obtain 1.60g of white solid powder. Yield: 48%, mp: 178-180°C, 1 H NMR (DMSO, 400MHz) δ: 0.92~0.97 (m, 3H, CH 3 ), δ: 1.5~1.6 (m, 2H, NHCH 2 CH 2 CH 3 ), δ: 3.2~3.3 (m, 2H, NHCH 2 CH 2 CH 3), δ: 7.5~7.6 (m, 2H, ArH), δ: 7.92~7.97 (m, 2H, ArH), δ: 8.29 (s, 1H, NHCH ...
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