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Synthetic method of benzanilide

A technology of phenylbenzamide and synthesis method, which is applied in the field of N-phenylbenzamide synthesis, can solve the problems of difficult reaction control, complicated reaction, complicated operation, etc., and achieves thorough reaction, few reaction by-products, and high conversion rate. high effect

Active Publication Date: 2019-01-08
LANZHOU PETROCHEM COLLEGE OF VOCATIONAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One is to use α, N-diphenylnitrone to react with acylating reagents such as benzoyl chloride, benzenesulfonyl chloride, phosphorus oxychloride and acetic anhydride (such as reaction formula B) to obtain N-phenylbenzamide. The acylating reagent required for the reaction has high activity, and it should be slowly added dropwise under cooling in an ice-water bath when feeding. After the dropwise addition, the reaction system must be heated to 100°C. Therefore, the method is complicated to operate and the reaction is difficult to control. The yield is low, especially when phosphorus oxychloride is used as an acylating reagent, the yield is only 6.5%
The other is to use α, N-diphenylnitrone and 2-phenyl-1-azolspiro[2.2]pent-1-ene to reflux reaction in benzene (such as reaction formula C), which can also be 39% The yield yields N-phenylbenzamide, however, the reaction has three products, the reaction is complex, and the yield is low

Method used

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  • Synthetic method of benzanilide
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  • Synthetic method of benzanilide

Examples

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Effect test

Embodiment 1

[0038] Example 1 A method for synthesizing N-phenylbenzamide, the method refers to dissolving the substrate α, N-diphenylnitrone and TBAF in a solvent, then adding alkali therein, and stirring and reacting at room temperature for 3 hours Finally, add water to quench the reaction to obtain a mixture; the mixture is extracted 3 times with ethyl acetate, the organic phases are combined, the organic phases are dried and concentrated under reduced pressure, and subjected to petroleum ether-ethyl acetate column chromatography to obtain a white solid N-phenylbenzamide, 57% yield.

[0039] Wherein: solvent refers to acetonitrile. The base refers to potassium hydroxide.

[0040] The mass volume ratio (g / mL) of α, N-diphenylnitrone to solvent is 1:140.

[0041] The mass ratio (g / g) of α, N-diphenylnitrone, TBAF, and base is 1:0.5:0.1.

[0042] The volume ratio (mL / mL) of petroleum ether to ethyl acetate in petroleum ether-ethyl acetate column chromatography is 10:1.

[0043] The con...

Embodiment 2

[0044] Example 2 A method for synthesizing N-phenylbenzamide, the method refers to dissolving the substrate α, N-diphenylnitrone and TBAF in a solvent, then adding alkali to it, and stirring and reacting at room temperature for 3 hours Finally, add water to quench the reaction to obtain a mixture; the mixture is extracted 3 times with ethyl acetate, the organic phases are combined, the organic phases are dried and concentrated under reduced pressure, and subjected to petroleum ether-ethyl acetate column chromatography to obtain a white solid N-phenylbenzamide, yield 62%.

[0045] Wherein: solvent refers to acetonitrile. The base refers to potassium hydroxide.

[0046] The mass volume ratio (g / mL) of α, N-diphenylnitrone to solvent is 1:140.

[0047] The mass ratio (g / g) of α, N-diphenylnitrone, TBAF, and base is 1:1:0.1.

[0048] Petroleum ether-ethyl acetate column chromatography is the same as in Example 1.

[0049] The conditions for concentrating under reduced pressure...

Embodiment 3

[0050] Example 3 A method for synthesizing N-phenylbenzamide, the method refers to dissolving the substrate α, N-diphenylnitrone and TBAF in a solvent, then adding alkali to it, and stirring and reacting at room temperature for 3 hours Finally, add water to quench the reaction to obtain a mixture; the mixture is extracted 3 times with ethyl acetate, the organic phases are combined, the organic phases are dried and concentrated under reduced pressure, and subjected to petroleum ether-ethyl acetate column chromatography to obtain a white solid N-phenylbenzamide, 65% yield.

[0051] Wherein: solvent refers to acetonitrile. The base refers to potassium hydroxide.

[0052] The mass volume ratio (g / mL) of α, N-diphenylnitrone to solvent is 1:140.

[0053] The mass ratio (g / g) of α, N-diphenylnitrone, TBAF, and base is 1:1.2:0.1.

[0054] Petroleum ether-ethyl acetate column chromatography is the same as in Example 1.

[0055] The conditions for concentrating under reduced pressu...

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Abstract

The invention relates to a synthetic method of benzanilide. The method comprises the following steps: alpha,N-diphenyl nitrone and TBAF as substrates are dissolved in a solvent, alkali is added to thesolution, the mixed solution is subjected to stirring reaction at room temperature for 2-5 h, water is added for quenching the reaction, and a mixture is obtained; extraction is performed on the mixture three times by ethyl acetate, organic phase is combined, dried, vacuum concentrated and subjected to petroleum ether-ethyl acetate column chromatography, and white solid benzanilide is obtained. The synthetic method has the advantages of mild reaction condition, simple operation, few reaction byproducts and high yield.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing N-phenylbenzamide. Background technique [0002] N-substituted phenyl benzamide compounds have a very wide range of biological activities, such as anti-inflammatory, antibacterial, anti-tumor, anti-arrhythmia and so on. As the simplest of these compounds, N-phenylbenzamide is a very important intermediate of medicine, pesticide and fragrance. Its general synthesis method (such as reaction formula A) is based on benzoic acid and aniline as raw materials. It is obtained by condensation reaction at 180~190 °C. The raw materials of this method are cheap and easy to obtain, but the reaction temperature is high and the operation is cumbersome. In addition, a method for synthesizing N-phenylbenzamide from α,N-diphenylnitrone has also been reported. One is to use α, N-diphenylnitrone to react with acylating reagents such as benzoyl chloride, benzene...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C233/65
CPCC07C231/10C07C233/65
Inventor 张怀远唐蓉萍石星丽王守伟张海亮颉林伍家卫吕维华
Owner LANZHOU PETROCHEM COLLEGE OF VOCATIONAL TECH
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