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Arylamidine compounds and synthetic method thereof

A synthesis method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as insufficient abundance

Active Publication Date: 2019-11-12
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Aryl amidines are one of the amidine compounds. At present, there are many researches on the agricultural activity of aryl amidines, but the aryl amidines researched so far are not rich enough. It is worthy of further research on the structure to find better effects. , antimicrobial active compounds with wider application range and more structural types

Method used

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  • Arylamidine compounds and synthetic method thereof
  • Arylamidine compounds and synthetic method thereof
  • Arylamidine compounds and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0177] Follow the steps below to synthesize aryl amidines:

[0178] 1) In a 50mL round-bottomed flask, mix 20mmoL of aniline and benzonitrile at a ratio of 1:1 and stir for 10 minutes, then add 1 equivalent of aluminum chloride in small amounts, heat to 200°C, and after 30 minutes Add 0.6mL of concentrated hydrochloric acid, 50mL of water, and 0.3g of activated carbon, continue stirring for 30 minutes, then stop stirring, cool to room temperature and filter, pour the filtered filtrate into a 100mL beaker containing 6.6g of sodium hydroxide and 36mL of water to produce floc, the floc is suction filtered, washed with water, and dried at room temperature to constant weight to obtain the aryl amidine;

[0179] 2) Put 0.2mmoL of compound 1, 1 equivalent of phenylpropynaldehyde, 1 equivalent of sodium benzenesulfinate, 1 equivalent of acetic acid, and 2 mL of ethanol in a 25 mL test tube, and react for 4 hours under a heating mantle at 70°C The reaction solution was obtained, extra...

Embodiment 2

[0342] Follow the steps below to synthesize aryl amidines:

[0343] 1) In a 50mL round bottom flask, mix aniline and benzonitrile for 8 minutes, then add aluminum trichloride several times in small amounts, heat to 180°C, add concentrated hydrochloric acid, water, and activated carbon after 20 minutes, and continue stirring Stop stirring after 20 minutes, filter after cooling to room temperature, pour the filtrate obtained by filtration into a 100mL beaker containing sodium hydroxide and water to produce flocs, wash the flocs by suction filtration, and dry at room temperature to constant weight to obtain The mass ratio of arylamidine, aniline, benzonitrile, aluminum trichloride, concentrated hydrochloric acid, water, activated carbon, and sodium hydroxide solution is 1:1.1:1.42:0.37:26.83:0.15:22.86, and the mass ratio of sodium hydroxide solution The concentration is 15.5%;

[0344] 2) Put compound 1, phenylpropynaldehyde, sodium benzenesulfinate, acetic acid, and ethanol in...

Embodiment 3

[0350] Follow the steps below to synthesize aryl amidines:

[0351] 1) In a 50mL round bottom flask, mix aniline and benzonitrile for 12 minutes, then add aluminum trichloride several times in small amounts, heat to 220°C, add concentrated hydrochloric acid, water, and activated carbon after 40 minutes, and continue stirring Stop stirring after 40 minutes, filter after cooling to room temperature, pour the filtrate obtained by filtration into a 100mL beaker containing sodium hydroxide and water to produce flocs, wash the flocs by suction filtration, and dry to constant weight at room temperature to obtain The mass ratio of aryl amidine, aniline, benzonitrile, aluminum trichloride, concentrated hydrochloric acid, water, activated carbon, sodium hydroxide solution is 1:1.12:1.44:0.39:26.85:0.17:22.88, the mass ratio of sodium hydroxide solution The concentration is 15.5%;

[0352] 2) Put compound 1, phenylpropynaldehyde, sodium benzenesulfinate, acetic acid, and ethanol in a 25...

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Abstract

The invention provides a synthetic method for arylamidine compounds. With the synthetic method provided by the invention, arylamidine is prepared by using aniline and benzonitrile as raw materials through a series of reactions; arylamidine compounds 4A to 4Z are prepared by a reaction of a compound 1 with phenylpropiolaldehyde, sodium benzene sulphinate, acetic acid and ethanol; arylamidine compounds 5A to 5M are prepared by a reaction of a compound 2 with a compound 9, a compound 3, acetic acid and ethanol; arylamidine compounds 6A to 6L are prepared by a reaction of a compound 4 with phenylpropiolaldehyde, sodium benzene sulphinate, tert-butyl hydroperoxide and acetonitrile; arylamidine compounds 6M to 6Z are prepared by a reaction of a compound 5 with a compound 6, a compound 7, tert-butyl hydroperoxide and acetonitrile; and an arylamidine compound 7A is prepared by a reaction of phenylpropiolaldehyde, a compound 8, acetonitrile and ethanol. The invention also provides the arylamidine compounds obtained by using the synthetic method provided by the invention. The synthetic method provided by the invention can synthesize the arylamidine compounds with various structures; and thearylamidine compounds all can be applied in the field of resisting of microorganisms.

Description

technical field [0001] The present invention relates to aryl amidine compound and its synthesis method. Background technique [0002] Amidines are nitrogen-substituted carboxylic acids and carboxylic acid ester analogs. Amidine compounds have good reactivity and coordination activity, and are important organic synthesis intermediates and good ligands. Amidine compounds have broad-spectrum antimicrobial activity, and can be used as anti-inflammatory, antibacterial, urinary and cardiovascular disease drugs, and some amidine compounds have good anticancer activity. Aryl amidines are one of the amidine compounds. At present, there are many researches on the agricultural activity of aryl amidines, but the aryl amidines researched so far are not rich enough. It is worthy of further research on the structure to find better effects. , Antimicrobial active compounds with wider application range and more structural types. Contents of the invention [0003] The technical problem to...

Claims

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Application Information

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IPC IPC(8): C07C257/18C07D233/64C07D409/12C07C315/00C07C317/24A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07C257/18C07C315/00C07D233/64C07D409/12C07C317/24
Inventor 曹华刘伟余跃
Owner GUANGDONG PHARMA UNIV
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