Fluorine-containing benzamide compound as well as preparation method and application thereof
A technology containing fluorine benzamide and fluorobenzamide, which is applied in organic chemistry, drug combination, blood diseases, etc., can solve the problems of few reports of benzamide compounds, achieve good anticoagulant activity, and be easy for industrial production and preparation The method is simple and efficient
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Embodiment 1
[0051] In this example, the target compound A was prepared by the following preparation method: Its preparation method is as follows:
[0052] (1) Add ethyl acrylate dropwise to the N,N-dimethylformamide organic solvent of p-fluoroaniline at room temperature, the molar ratio of p-fluoroaniline to ethyl acrylate is 1:1.1, and add An appropriate amount of diethylamine was reacted at room temperature for 3 hours to obtain compound 1, and the reaction formula was as follows:
[0053]
[0054] (2) 3-nitro-4-chloro-benzoic acid and hydroxylamine aqueous solution were reacted for 2 hours at a temperature of 40° C., wherein the molar ratio of 3-nitro-4-chloro-benzoic acid to hydroxylamine was 1:1.2 to obtain 3-nitro-4-hydroxylamino-benzoic acid compound, the reaction formula is as follows:
[0055]
[0056] (3) 3-nitro-4-hydroxyamino-benzoic acid compound and thionyl chloride were reacted in dichloromethane solvent at 70°C for 8 hours at a molar ratio of 1:1.1 under the actio...
Embodiment 2
[0062] In this example, the target compound B was prepared by the following preparation method: Its preparation method is as follows:
[0063] (1) Add ethyl acrylate dropwise to the N,N-dimethylformamide organic solvent of 3-fluoromethylaniline at room temperature, the molar ratio of 3-fluoromethylaniline to ethyl acrylate is 1 : 1.2, and add an appropriate amount of diethylamine in the reaction, react at room temperature for 5 hours, obtain compound 2, and the reaction formula is as follows:
[0064]
[0065] (2) 3-nitro-4-chloro-benzoic acid and hydroxylamine aqueous solution were reacted for 1 hour at a temperature of 50° C., wherein the molar ratio of 3-nitro-4-chloro-benzoic acid to hydroxylamine was 1:1.3 to obtain 3-nitro-4-hydroxylamino-benzoic acid compound, the reaction formula is as follows:
[0066]
[0067] (3) 3-nitro-4-hydroxyamino-benzoic acid compound and thionyl chloride react at 60°C in dichloromethane solvent under the action of catalyst benzyltrie...
Embodiment 3
[0073] In this example, the target compound C was prepared by the following preparation method: Its preparation method is as follows:
[0074] (1) Add ethyl acrylate dropwise to the N,N-dimethylformamide organic solvent of the aniline compound shown in formula II at room temperature, the molar ratio of the aniline compound shown in formula II to ethyl acrylate is 1:1.3 , and add an appropriate amount of diethylamine to the reaction, and react at room temperature for 8 hours to obtain compound 3, the reaction formula is as follows:
[0075]
[0076] (2) 3-nitro-4-chloro-benzoic acid and hydroxylamine aqueous solution were reacted for 2 hours at a temperature of 40° C., wherein the molar ratio of 3-nitro-4-chloro-benzoic acid to hydroxylamine was 1:1.2 to obtain 3-nitro-4-hydroxylamino-benzoic acid compound, the reaction formula is as follows:
[0077]
[0078] (3) 3-nitro-4-hydroxyamino-benzoic acid compound and thionyl chloride were reacted in dichloromethane solvent ...
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