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Method for synthesizing 2-benzamido-3-aryl acrylate

A technology of aryl acrylate and benzoyl, which is applied in the field of synthesis of 2-benzamido-3-aryl acrylate, can solve the problems of long reaction time, complicated operation, low yield, etc., and achieve shortening Effects of reaction time, increased yield, ease of handling and control

Inactive Publication Date: 2017-05-10
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are problems such as complex operation, long reaction time and low yield in the above synthetic methods

Method used

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  • Method for synthesizing 2-benzamido-3-aryl acrylate
  • Method for synthesizing 2-benzamido-3-aryl acrylate

Examples

Experimental program
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Effect test

example 1

[0021] Under the protection of argon, 0.1 mol (10.6 g) of benzaldehyde, 0.1 mol (19.2 g) of methyl hippurate, 0.1 mol (24.6 g) of cesium trifluoroacetate, and 100 mol of acetic anhydride were successively added to a dry 500 mL three-necked flask. mL, control the reaction temperature at 100°C, stir the reaction for 8 h, and detect that the reaction is complete, add 250 mL of water and stir to quench the reaction, extract twice with 100 mL of dichloromethane, separate and combine the dichloromethane layer, and use 100 mL ×2 washed with water, dried overnight with 15 g of anhydrous magnesium sulfate, filtered, recovered the solvent under reduced pressure to obtain a tan solid, and recrystallized from methanol to obtain 24.3 g of an off-white solid with a purity of 98.4% and a yield of 86.4%. 1 H NMR (400 MHz, DMSO- d 6 ) δ : 3.74(s, 3H), 7.35~7.44(m, 4H), 7.52~7.63(m,3H), 7.69(d, J =7.2Hz, 2H), 8.00(d, J =7.2Hz, 2H), 10.14(s, 1H). 13 C NMR (100MHz, DMSO- d 6 ) δ : 166.2, ...

example 2

[0023] Under the protection of argon, 0.105 mol (19.4 g) of 4-bromobenzaldehyde, 0.1 mol (19.2 g) of methyl hippurate, 0.1 mol (8.2 g) of sodium acetate, and 0.1 mol (8.2 g) of sodium acetate were added successively to a dry 500 mL three-necked flask 100 mL, control the reaction temperature at 110 °C, stir the reaction for 7 h, and detect the completion of the reaction in the liquid phase, add 250 mL of water and stir to quench the reaction, extract twice with 100 mL of dichloromethane, separate and combine the dichloromethane layer, and use 100 mL×2 washed with water, dried overnight with 15 g of anhydrous magnesium sulfate, filtered, and the solvent was recovered under reduced pressure to obtain a tan solid, which was recrystallized from methanol to obtain 30.2 g of an off-white solid with a purity of 98.6% and a yield of 83.8%. 1 H NMR (400 MHz, DMSO- d 6 ) δ : 3.75(s, 3H), 7.41(s, 1H), 7.53~7.63(m, 7H), 8.00(d, J =7.6Hz, 2H), 10.16(s, 1H). 13 C NMR (100MHz, DMSO- d 6...

example 3

[0025] Under argon protection, 0.1 mol (15.1 g) of p-nitrobenzaldehyde, 0.1 mol (19.2 g) of methyl hippurate, 0.1 mol (8.2 g) of sodium acetate, and acetic anhydride 105 mL, control the reaction temperature at 95 ° C, stir the reaction for 5.5 h, the liquid phase detection reaction is complete, add 250 mL of water and stir to quench the reaction, extract twice with 100 mL of dichloromethane, separate and combine the dichloromethane layer, and use 100 mL×2 washed with water, dried overnight with 15 g of anhydrous magnesium sulfate, filtered, and the solvent was recovered under reduced pressure to obtain a tan solid, which was recrystallized from methanol to obtain 27.6 g of an off-white solid with a purity of 98.4% and a yield of 84.6%. 1 H NMR (400 MHz, DMSO- d 6 ) δ : 3.77(s, 3H), 7.45(s, 1H), 7.55(t, J =7.6Hz,2H), 7.63(t, J =7.4Hz, 1H), 7.90(d, J =8.8Hz, 2H), 7.98(d, J =7.6Hz, 2H), 8.26(d, J =8.8Hz, 2H), 10.31(s, 1H). 13 C NMR (100MHz, DMSO- d 6 ) δ : 166.3, 165.2...

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Abstract

The invention discloses a method for preparing 2-benzamido-3-aryl acrylate, and belongs to the field of organic chemical synthesis. The method is mainly implemented by the following steps: adding aromatic aldehyde, ethylhippurate, acetic anhydride and an alkali catalyst into a three-mouth flask according to a certain proportion under the protection of argon, and performing condensation reaction under a certain temperature condition to obtain a 2-benzamido-3-aryl acrylate compound by one step. According to the method, production steps are shortened, the method is easy to operate and control, the production operation environment is improved, the yield and the quality of a product are improved, and the reaction time is shortened; the 2-benzamido-3-aryl acrylate is mainly used for evaluation of the activity of a chiral ligand and catalyst thereof, medicinal synthesis, a pesticide, a photoelectric material and the like.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 2-benzamido-3-aryl acrylate, especially 2-benzamido-3-aryl acrylate, 2-benzamido-3-aryl The synthesis of ethyl acrylate belongs to the field of organic chemistry. Background technique [0002] 2-Benzamido-3-aryl acrylate is an important organic intermediate, which is mainly used to evaluate the activity of chiral phosphorus ligands and their catalysts, pharmaceutical synthesis, pesticides and optoelectronic materials, etc. At present, the synthesis method of 2-benzoyl-3 aryl acrylate mainly uses aromatic aldehydes and hippuric acid as raw materials, obtains oxazolone compound intermediates through Erlenmeyer reaction, and then obtains 2-benzene formyl-3-aryl acrylic acid, and then esterify to obtain 2-benzamido-3-aryl acrylate; or use aromatic aldehydes and hippuric acid as raw materials to obtain oxazolone compound intermediates through Erlenmeyer reaction, Then, 2-benzamido-3-aryl acryl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C233/87
CPCC07C231/12C07C233/87
Inventor 陈海涛王文新段显英李继蒋卫鹏韩福娇
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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