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Chemical synthesis process of 2-hydrixy-5-amudo benzophenone compounds

A technology for the chemical synthesis of amidophenone, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve the problems of large amount of catalyst aluminum trichloride, low product yield and purity, and difficult post-treatment, etc. problems, and achieve the effects of low production cost, no three wastes, and mild reaction conditions

Inactive Publication Date: 2006-04-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional Lewis acids such as aluminum trichloride can be used as catalysts to improve reaction efficiency under mild conditions, and have been widely used in organic synthesis. However, the disadvantage of this production process is that the amount of catalyst aluminum trichloride is large, because most of the traditional Lewis acid decomposes with water and fails, the reaction must be strictly controlled under anhydrous conditions, and for nitrogen-containing or imine compounds, nitrogen atoms will inhibit the catalytic activity of Lewis acid, a large amount is required to meet the reaction, and there are three wastes Disadvantages such as large amount, difficult post-processing, low product yield and purity

Method used

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  • Chemical synthesis process of 2-hydrixy-5-amudo benzophenone compounds
  • Chemical synthesis process of 2-hydrixy-5-amudo benzophenone compounds
  • Chemical synthesis process of 2-hydrixy-5-amudo benzophenone compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0029] The feed ratio is 4-alkoxybenzamide: acid halide: ytterbium trifluoromethanesulfonate is 1:1:0.02 (molar ratio), 4-alkoxybenzamide is 4-methoxyphenylacetamide, acid halide Acetyl chloride, methylene chloride is used as an organic solvent, and its consumption is 10 times of the quality of 4-methoxyphenylacetamide.

[0030] In a 150ml four-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 75mmol of 4-methoxybenzamide, dissolve it with 124g of dichloromethane, add 75mmol of acid halide and 1.5mmol of ytterbium trifluoromethanesulfonate at room temperature mmol, after addition, the temperature was raised to 40° C., and reacted at 40 to 45° C. for 2 hours, while tracking and monitoring with HPLC (flow rate: 1.5 ml / min, acetonitrile: water: acetic acid=20: 80: 0.1), the reaction was completed, evaporated Remove the solvent, and slowly add 100ml of ice water under ice-bath cooling, stir continuously for 10min, and filter.

[0031] The filtr...

Embodiment 2

[0034] Feeding ratio is 4-alkoxybenzamide: acyl halide: ytterbium trifluoromethanesulfonate is 1: 2: 0.02 (molar ratio), 4-alkoxybenzamide is 4-methoxyphenylacetamide, feed amount Acid halide is acetyl chloride, and the charging amount is 150mmol; Ytterbium trifluoromethanesulfonate consumption is 1.5mmol; Dichloromethane is used as organic solvent, and its consumption is 99g, i.e. 8 times of 4-methoxyphenylacetamide quality .

[0035] Other operations are the same as in Example 1, the product yield is 84.2%, the purity is 99.6%, the melting point is 166.3-167.0°C, and the recovery rate of ytterbium trifluoromethanesulfonate is 94%.

Embodiment 3

[0037] Feeding ratio is 4-alkoxybenzamide: acyl halide: ytterbium trifluoromethanesulfonate is 1: 4: 0.02 (molar ratio), 4-alkoxybenzamide is 4-methoxyphenylacetamide, feed amount It is 75mmol; Acyl halide is acetyl chloride, and the charging amount is 300mmol; Dichloromethane is used as the organic solvent, and its consumption is 99g, i.e. 8 times of the quality of 4-methoxyphenylacetamide, and the consumption of ytterbium trifluoromethanesulfonate is 1.5mmol .

[0038] Other operations are the same as in Example 1, the product yield is 86.3%, the purity is 99.8%, the melting point is 166.5-167.3°C, and the recovery rate of ytterbium trifluoromethanesulfonate is 95%.

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Abstract

A process for chemically synthesizing 2-hydroxy-5-amidophenylone compounds as an important intermediate for medicines or agricultural chemicals includes reacting between 4-alkoxy phenylamide and acid halide in organic solvent under existance of ytterbium trifluoro methanesulfonate, and separating product by an optimized method. Its advantages are high output rate and purity, less consumption of catalyst, and basically no pollution.

Description

(1) Technical field [0001] The present invention relates to a kind of trifluoromethanesulfonic acid ytterbium [Yb (OTf) 3 ] replace traditional Lewis acids such as aluminum trichloride to prepare the chemical synthesis method of 2-hydroxyl-5-amidobenzophenone compounds. This series of products are widely used in the synthesis of pesticides, medicines and dyes, and have high practical value. (2) Background technology [0002] Before the present invention was made, the chemical synthesis method of 2-hydroxy-5-amidobenzophenone compounds in the prior art was prepared by using traditional Lewis acids such as aluminum trichloride as catalysts. As proposed in US 5,484,923, it is prepared by reacting 0.12mol 4-methoxyphenylacetamide and 0.42mol acetyl chloride under the catalysis of 0.41mol aluminum trichloride. [0003] Traditional Lewis acids such as aluminum trichloride can be used as catalysts to improve reaction efficiency under mild conditions, and have been widely used in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/33C07C231/12
Inventor 苏为科金灿
Owner ZHEJIANG UNIV OF TECH