Isoxazoline substituted benzamide derivative as well as preparation method and application thereof
A methyl and fluorinated technology, applied in the direction of botany equipment and methods, applications, biocides, etc.
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Embodiment 1
[0142] Example 1: N-(cyanomethyl)-N-cyclopropyl-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroiso Preparation of oxazol-3-yl)-2-methylbenzamide (compound 1)
[0143]
[0144] The first step reaction: the preparation of (Z)-4-((oxime) methyl)-2-methylbenzoate: at room temperature, 26.70g (0.15mol) 4-formyl-2-methyl Methyl benzoate, 12.53g (0.18mol) of hydroxylamine hydrochloride, and 18.45g (0.225mol) of sodium acetate were dissolved in a mixed solution of 75ml of water and 300ml of ethanol. The reaction was stirred for 6 hours. The reaction mixture was concentrated, diluted with ethyl acetate and aqueous sodium hydroxide (2M), and the phases were separated. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Suction filtration and drying yielded 25.76 g of the product, with a yield of 89%.
[0145] LC-MS[M+H] + =194.08, [M+Na] + =216.06, [M+K] + = 232.03.
[0146] The second step reaction: the preparation of 1,3-dich...
Embodiment 2
[0156] Example 2: N-(cyanomethyl)--4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3- base)-N-(2,2-difluoroethyl)-2-methylbenzamide (compound 5)
[0157]
[0158] The first step reaction: Preparation of 2-((2,2-difluoroethyl)amino)acetonitrile: 2.43g (0.03mol) 2,2-difluoroethylamine, 3.0g (0.025mol) bromoacetonitrile at room temperature 1. Add 20ml of acetonitrile into the three-necked flask, and stir and react at 60°C for 8 hours. The reaction solution was desolvated under reduced pressure. 60 ml of water were added to the residue, extracted with ethyl acetate (3*20 ml), and the organic phases were combined. Wash with saturated saline. Dry over anhydrous magnesium sulfate. The solvent was removed from the organic phase under reduced pressure to obtain 2.46 g of the product, with a yield of 82%.
[0159] The second step reaction: N-(cyanomethyl)--4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3 -yl)-N-(2,2-difluoroethyl)-2-methyl...
Embodiment 3
[0162] Example 3: N-(cyanomethyl)-N-cyclopropyl-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5 -Preparation of -dihydroisoxazol-3-yl)-2-methylbenzamide (compound 13)
[0163]
[0164]The first step reaction: the preparation of (Z)-4-((oxime) methyl)-2-methylbenzoate: at room temperature, 26.70g (0.15mol) 4-formyl-2-methyl Methyl benzoate, 12.53g (0.18mol) of hydroxylamine hydrochloride, and 18.45g (0.225mol) of sodium acetate were dissolved in a mixed solution of 75ml of water and 300ml of ethanol. The reaction was stirred for 6 hours. The reaction mixture was concentrated, diluted with ethyl acetate and aqueous sodium hydroxide (2M), and the phases were separated. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Suction filtration and drying yielded 25.76 g of the product, with a yield of 89%.
[0165] LC-MS[M+H] + =194.08, [M+Na] + =216.06, [M+K] + = 232.03.
[0166] The second step reaction: the preparation of...
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