Method for producing 2-halogenated benzamides
A technology of halogenated benzamides and benzamides, applied in the field of preparing 2-halogenated benzamide compounds, can solve problems such as neither description nor suggestion, and achieves the effect of low cost
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Embodiment 1
[0108] Preparation of 2-iodo-6-methyl-N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]benzamide
[0109] At 70°C, 2-methyl-N-[1,1-dimethyl-2-(methylthio)ethyl]benzamide (2.37 g), tetrahydrofuran (20 ml), N-iodosuccinate A mixture of imide (2.30 g) and palladium acetate (0.22 g) was stirred and heated for 2 hours. The solvent was distilled off under reduced pressure, and the obtained concentrate was dissolved in 1,2-dichloroethane (20 mL). The resulting solution was washed with aqueous sodium thiosulfate solution and water, and the obtained solution containing 2-iodo-6-methyl-N-[1,1-dimethyl-2-(methylthio)ethyl] The organic layer of benzamide was used as such in the next step. To this solution were added acetic acid (0.60 g) and concentrated sulfuric acid (0.20 g), and to the resulting mixture was added 35% hydrogen peroxide (1.17 g). After stirring at 60° C. for 1 hour, 35% hydrogen peroxide (1.46 g) was added dropwise thereto at the same temperature, and stirred for 3 hours. Then...
Embodiment 2
[0112] Preparation of N 2 -[1,1-Dimethyl-2-(methyl-sulfonyl)ethyl]-3-iodo-N 1 -(2-Methyl-4-pentafluoroethyl-phenyl)-1,2-phthalamide
[0113] At 70°C, the N 2 -[1,1-Dimethyl-2-(methylthio)ethyl]-N 1 -(2-Methyl-4-pentafluoroethylphenyl)-1,2-phthalamide (2.37 g), THF (20 mL), N-iodosuccinimide (1.13 g) and acetic acid The mixture of palladium (0.11 g) was stirred and heated for 2 hours. The solvent was distilled off under reduced pressure, and the obtained concentrate was dissolved in 1,2-dichloroethane (20 mL). The resulting solution was washed with aqueous sodium thiosulfate and water, and the N-containing 2 -[1,1-Dimethyl-2-(methylsulfinyl)ethyl]-3-iodo-N 1 The organic layer of -(2-methyl-4-pentafluoroethylphenyl)-1,2-phthalamide was used as it was in the subsequent step. To the solution were added acetic acid (0.30 g) and concentrated sulfuric acid (0.10 g), and to the resulting mixture was added 35% hydrogen peroxide (0.58 g). After stirring at 60° C. for 1 hour, 35%...
Embodiment 3
[0116] Preparation of N 2 -[1,1-Dimethyl-2-(methyl-sulfonyl)ethyl]-3-iodo-N 1 -(2,3,4-Trichlorophenyl)-1,2-phthalamide
[0117] At 80°C, the N 2 -[1,1-Dimethyl-2-(methyl-sulfinyl)ethyl]-N 1 -(2,3,4-Trichlorophenyl)-1,2-benzenedicarboxamide (195.0 g), N,N-dimethylacetamide (780 ml), 1,3-diiodo-5 , a mixture of 5-dimethylhydantoin (91.44 g) and palladium acetate (1.90 g) was stirred and heated for 3 hours. The solvent was distilled off under reduced pressure, and the obtained concentrate was dissolved in 1,2-dichloroethane (780 mL). The resulting solution was washed with aqueous sodium thiosulfate and water, and the N-containing 2 -[1,1-Dimethyl-2-(methyl-sulfinyl)ethyl]-3-iodo-N 1 The organic layer of -(2,3,4-trichlorophenyl)-1,2-phthalamide was used as it was in the subsequent step. To this solution were added formic acid (19.44 g) and concentrated sulfuric acid (16.57 g) at 60°C, and 35% hydrogen peroxide (49.25 g) was added dropwise to the resulting mixture. After st...
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