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Synthetic method of substituted benzamidine compound

A synthetic method and compound technology, applied in organic chemistry and other fields, can solve the problems of long synthetic route and complicated preparation of raw materials, and achieve the effects of low production cost, easy operation of reaction and few by-products

Inactive Publication Date: 2014-02-12
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The object of the present invention provides a kind of synthetic method of substituted benzamidine compound in order to solve technical problems such as above-mentioned raw material preparation complexity, synthetic route is long, and this synthetic method has reaction condition milder, synthetic step is shorter, and final obtained The substituted benzamidine compounds have the characteristics of high purity and high yield

Method used

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  • Synthetic method of substituted benzamidine compound
  • Synthetic method of substituted benzamidine compound
  • Synthetic method of substituted benzamidine compound

Examples

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Comparison scheme
Effect test

Embodiment 1

[0045] A kind of synthetic method of substituted benzamidine compound, the structural formula of described substituted benzamidine compound is as follows:

[0046]

[0047] where G is H;

[0048] Both R1 and R2 are ethyl groups.

[0049] The synthetic method of above-mentioned substituted benzamidine compound, specifically comprises the following steps:

[0050] (1) In 20ml of organic solvent, mix 1g of intermediate II with 1.35g of POCl 3 In the presence of 2.30 g of alkali, control the reaction temperature to 40° C. and carry out the reaction for 1 h to obtain a solution containing intermediate III;

[0051] Described organic solvent is toluene;

[0052] Described alkali is triethylamine;

[0053] The general structural formula of the intermediate II is:

[0054] , where G is H;

[0055] Intermediate II, POCl used in the reaction process 3 , the amount of alkali and organic solvent, according to intermediate II: POCl 3 : Alkali: organic solvent is calculated acc...

Embodiment 2

[0066] A kind of synthetic method of substituted benzamidine compound, the structural formula of described substituted benzamidine compound is as follows:

[0067]

[0068] Wherein G is 4-methyl;

[0069] Both R1 and R2 are ethyl groups.

[0070] The synthetic method of above-mentioned substituted benzamidine compound, specifically comprises the following steps:

[0071] (1) In 10ml of organic solvent, mix 0.5g of intermediate II with 0.74g of POCl 3 In the presence of 2.46 g of alkali, control the reaction temperature to 50° C. and carry out the reaction for 0.5 h to obtain a solution containing intermediate III;

[0072] Described organic solvent is benzene;

[0073] Described alkali is diisopropylamine;

[0074] The general structural formula of the intermediate II is:

[0075] , wherein G is 4-methyl;

[0076] Intermediate II, POCl used in the reaction process 3 , the amount of alkali and organic solvent, according to intermediate II: POCl 3 : Alkali: organic ...

Embodiment 3

[0087] A kind of synthetic method of substituted benzamidine compound, the structural formula of described substituted benzamidine compound is as follows:

[0088]

[0089] Wherein G is 4-Cl;

[0090] R1 and R2 form a six-membered ring with the nitrogen atom to which they are attached:

[0091] .

[0092] The synthetic method of above-mentioned substituted benzamidine compound, specifically comprises the following steps:

[0093] (1) In 10ml of organic solvent, mix 0.5g of intermediate II with 0.98g of POCl 3 In the presence of 1.79 g of base, control the reaction temperature to 40° C. and carry out the reaction for 1 h to obtain a solution containing intermediate III;

[0094] Described organic solvent is xylene;

[0095] Described alkali is triethylamine;

[0096] The general structural formula of described intermediate II p-chloroformanilide is:

[0097] , wherein G is 4-Cl;

[0098] Intermediate II, POCl used in the reaction process 3 , the amount of alkali ...

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Abstract

The invention discloses a synthetic method of a benzamidine compound. The synthetic method comprises the following steps of: taking the formanilide as the raw material, adding phosphorus oxychloride and an acid-binding agent triethylamine or diisopropylamine, and reacting to obtain corresponding isonitrile, directly adding Cu2O and diethylamine, or Cu2O and piperidine to the reaction liquid directly without separation, continuing to react, standing the reaction liquid for layering, extracting the oil layer, extracting the obtained water layer by using ethyl acetate and then extracting the oil layer, blending the two oil layers obtained and removing the ethyl acetate through spiral flashing, carrying out column chromatography, removing a solvent through spiral flashing, thus obtaining an oily liquid at last, namely the benzamidine compound. The synthetic method is simple in reaction process and moderate in reaction conditions, and the yield of the synthetic method is above 70%.

Description

technical field [0001] The invention relates to a method for synthesizing substituted benzamidine compounds. Background technique [0002] Amidines are nitrogen-substituted carboxylic acid analogs, and amidine compounds are fragments of some physiologically active substances, and are important synthetic intermediates in organic synthesis. Amidines are very important compounds widely used in antibiotics, diuretics, anti-inflammatory drugs, insect repellents and broad-spectrum acaricides. It can also be used in the preparation of nitrogen heterocyclic compounds, and is now attracting more and more attention. DuPont has disclosed the use of aryl amidines as fungicides. The effectiveness of the amidines described in the prior art is good, but the synthesis method is complicated and the cost is high. [0003] The more commonly used synthetic methods are as follows: [0004] Method 1: Amide acetal method [0005] [0006] The synthesis method of amide acetal is COF 2 , S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/12
Inventor 杜葩
Owner SHANGHAI INST OF TECH
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