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Method for preparing N-aryl amido formyl phosphonate through anode oxidization

An aryl carbamoyl phosphonate, anodic oxidation technology, applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of inability to realize the reaction, meet the requirements of avoiding use, mild reaction conditions, and convenient operation Effect

Inactive Publication Date: 2018-12-11
NORTHWEST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the disadvantage of this method is that it needs to use an excessive amount of iodine simple substance, and the reaction promoted by catalytic amount of iodine cannot be realized.

Method used

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  • Method for preparing N-aryl amido formyl phosphonate through anode oxidization
  • Method for preparing N-aryl amido formyl phosphonate through anode oxidization
  • Method for preparing N-aryl amido formyl phosphonate through anode oxidization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1, the preparation of dimethyl (p-tolylcarbamoyl) phosphonate

[0021] In a three-necked flask, add 10 mL of methanol, 0.3 mmol of lithium perchlorate, 10 mol% of tetrabutylammonium iodide, and 0.2 mmol of N-phenylphosphoric carboxamide in sequence. Stir at room temperature, and use a platinum sheet as an electrode. Electrolyze at a constant current for about 2 h at I = 10 mA (until the reaction solution changes from colorless to light yellow); after the reaction is detected by TCL, add 2 mL of saturated ammonium chloride to quench the reaction, and use an excess (3×15 mL) of ethyl acetate was extracted quickly, dried over anhydrous magnesium sulfate, and separated by column chromatography (eluent was ethyl acetate:petroleum ether=1:2) to obtain the pure product——dimethyl (p-tolyl carbamoyl) phosphonate. Yield 92%. Its synthetic formula is as follows:

[0022]

[0023] 1 H NMR (600 MHz, CDCl 3 ) δ=8.87 (s, 1H), 7.63 (d, J = 8.4Hz, 2H), 7.35(t, J =...

Embodiment 2

[0024] Embodiment 2: the preparation of diethyl ((4-methoxyphenyl) carbamoyl) phosphonate

[0025] In a three-necked flask, add 10 mL ethanol, 0.3 mmol lithium perchlorate, 10 mol% tetrabutylammonium iodide, 0.2 mmol N-(4-methoxyphenyl)phosphorocarboxamide, and stir at room temperature Then, use platinum sheet as electrode, and conduct constant current electrolysis at I = 10 mA for about 2 h (until the reaction solution changes from colorless to light yellow); after the reaction is detected by TCL, 2 mL of saturated ammonium chloride is added to quench the reaction. The reaction was quickly extracted with excess (3×15 mL) ethyl acetate, dried over anhydrous magnesium sulfate, and separated by column chromatography (eluent: ethyl acetate:petroleum ether=1:2) to obtain the pure product— - Diethyl((4-methoxyphenyl)carbamoyl)phosphonate. Yield 85%. Its synthetic formula is as follows:

[0026]

[0027] 1 H NMR (600 MHz, CDCl 3 ) δ=8.90 (s, 1H), 7.55 (d, J = 1.2Hz, 2H), 6...

Embodiment 3

[0028] Embodiment 3: Preparation of diisopropyl (o-tolylcarbamoyl) phosphonate

[0029] In a three-necked flask, 10 mL of isopropanol, 0.3 mmol of lithium perchlorate, 10 mol% of tetrabutylammonium iodide, 0.2 mmol of N-(2-methyl-phenyl)phosphorocarboxamide were added successively, and Stir at room temperature, use a platinum sheet as an electrode, and conduct constant current electrolysis at I = 10mA for about 2 h (until the reaction solution changes from colorless to light yellow); after the reaction is detected by TCL, add 2 mL of saturated ammonium chloride to quench the reaction. Reaction, rapid extraction with excess (3×15mL) ethyl acetate, drying over anhydrous magnesium sulfate, separation by column chromatography (eluent: ethyl acetate:petroleum ether=1:2), to obtain the pure product—— Diisopropyl(o-tolylcarbamoyl)phosphonate. The yield is 80%. Its synthetic formula is as follows:

[0030]

[0031] 1 H NMR (600 MHz, CDCl 3 ) δ= 8.64 (s, 1H), 7.94 (d, J = 7.8...

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Abstract

The invention provides a method for preparing N-aryl amido formyl phosphonate through anode oxidization. The method is characterized in that N-aryl phosphate formamide is taken as a raw material, alcohol is taken as a solvent and a cathode reactant, tetrabutylammonium iodide is taken as a catalyst, lithium perchlorate is taken as electrolyte, and a platinum sheet is taken as an electrode to perform anode oxidization reaction. The method uses tetrabutylammonium iodide as the catalyst, I 2 is generated in situ by I-negative ions during anode oxidization to participate in reaction of activating N-aryl phosphate formamide and alcohol to generate a product; I2 is reduced into I-negative ions; under an electric-oxidization reducing conditions, the I-negative ions realize regeneration and cyclicuse of the I-negative ions to I2, so that using requirements of excessive I2 are avoided, and the process is simple, reaction conditions are gentle, the cost is low and the yield is high; the cheap alcohol is the reactant, and is also used as the solvent, so that a medium is provided for reaction, and the alcohol is also used as the cathode reactant, and therefore, pollution, on environment, is reduced.

Description

technical field [0001] The invention relates to a preparation method of N-aryl carbamoyl phosphonate, in particular to a method for preparing N-aryl carbamoyl phosphonate by anodic oxidation, which belongs to the field of organic synthesis chemistry. Background technique [0002] Organophosphorus compounds are closely related to human life. They are involved in nucleic acids, coenzymes, organophosphate nerve gases, organophosphate insecticides, organophosphate herbicides, chemotherapeutic agents, plasticizers, antioxidants, surfactants, complexing agents, It is widely used in organic phosphorus extractant, flotation agent and flame retardant. Organic phosphonates and their derivatives are an important class of compounds in various fields, especially medicinal chemistry, materials chemistry, agricultural chemistry, and catalysis. For example, phosphonates and carbamoylphosphonates are matrix metalloproteinase (MMP) inhibitors, anti-metastatic and antineoplastic agents. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 权正军武秋丽武永辉王喜存
Owner NORTHWEST NORMAL UNIVERSITY
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