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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  • Description
  • Claims
  • Application Information

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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 meth

Method used

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  • Synthetic method of benzanilide
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  • Synthetic method of benzanilide

Examples

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Example Embodiment

[0038] Example 1 A method for the synthesis of N-phenylbenzamide, which refers to dissolving the substrate α,N-diphenylnitrone and TBAF in a solvent, and then adding an alkali to it, and stirring and reacting for 3 hours at room temperature Then, the reaction was quenched by adding water to obtain a mixture; after the mixture was extracted with ethyl acetate for 3 times, the organic phases were combined, the organic phases were dried, concentrated under reduced pressure, and subjected to petroleum ether-ethyl acetate column chromatography to obtain a white solid The yield of N-phenylbenzamide was 57%.

[0039] Among them: solvent refers to acetonitrile. Alkali refers to potassium hydroxide.

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

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

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

Example Embodiment

[0044] Example 2 A method for the synthesis of N-phenylbenzamide, which refers to dissolving the substrate α,N-diphenylnitrone and TBAF in a solvent, then adding an alkali to it, and stirring and reacting for 3 hours at room temperature Then, the reaction was quenched by adding water to obtain a mixture; after the mixture was extracted with ethyl acetate for 3 times, the organic phases were combined, the organic phases were dried, concentrated under reduced pressure, and subjected to petroleum ether-ethyl acetate column chromatography to obtain a white solid The yield of N-phenylbenzamide was 62%.

[0045] Among them: solvent refers to acetonitrile. Alkali refers to potassium hydroxide.

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

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

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

[0049] The conditions for concentration under...

Example Embodiment

[0050] Example 3 A method for the synthesis of N-phenylbenzamide. The method refers to dissolving the substrate α,N-diphenylnitrone and TBAF in a solvent, adding an alkali to it, and stirring and reacting at room temperature for 3 hours Then, the reaction was quenched by adding water to obtain a mixture; after the mixture was extracted with ethyl acetate for 3 times, the organic phases were combined, the organic phases were dried, concentrated under reduced pressure, and subjected to petroleum ether-ethyl acetate column chromatography to obtain a white solid The yield of N-phenylbenzamide is 65%.

[0051] Among them: solvent refers to acetonitrile. Alkali refers to potassium hydroxide.

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

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

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

[0055] The conditions for concentration unde...

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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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