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Paradiethylamino methylene amine propyl benzoate compound and preparation method thereof

A technology of propyl diethylaminomethylaminobenzoate and propyl formamidobenzoate is applied in the field of propyl p-diethylaminomethylaminobenzoate compound and preparation thereof, and can solve the problem of high carcinogenicity and achieve The effect of low toxicity, mild reaction conditions and few steps

Inactive Publication Date: 2015-02-11
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Dimeform, N-(4-chloro-o-tolyl)-N,N-dimethylformamidine, is a high-efficiency broad-spectrum organic nitrogen agricultural insecticide and acaricide, which is effective against organophosphorus, organochlorine and amino Formic ester insecticides are effective in resistant insects and are moderately toxic, but the carcinogenicity of its metabolite 4-chloro-o-methylaniline is 10 times higher than that of the parent compound

Method used

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  • Paradiethylamino methylene amine propyl benzoate compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A preparation method of propyl-diethylaminomethenylaminobenzoate, specifically comprising the steps of:

[0024] (1) Add 0.5g (0.0024mol) propyl 4-formylaminobenzoate to a 25mL round bottom flask, add 10mL of organic solvent, then add 1.71g of alkali, stir, and drop in 0.41g of POCl 3 , control the temperature to 90°C, and react for 0.25h to obtain a propyl p-isocyanobenzoate solution;

[0025] Described organic solvent is toluene;

[0026] Described alkali is diisopropylamine;

[0027] Propyl p-formamidobenzoate, POCl used in the reaction process 3 , the amount of alkali and organic solvent, according to propyl p-formamidobenzoate: POCl 3 : Alkali: organic solvent is calculated according to the ratio of 1mol: 1.1mol: 7mol: 4.17L;

[0028] (2), in the propyl p-isocyanobenzoate solution obtained in step (1), add 0.26g diethylamine and 0.035g Cu 2 0, the temperature was controlled at 100°C for 14 hours of reaction. After the obtained reaction solution was allowed to ...

Embodiment 2

[0036] (1) Add 0.5g of propyl 4-formylaminobenzoate to a 25mL round bottom flask, add 10mL of organic solvent, then add 0.74g of alkali, stir, and drop in 0.56g of POCl 3 , control the temperature at 50°C, and react for 4 hours to obtain a propyl p-isocyanobenzoate solution;

[0037] Described organic solvent is benzene;

[0038] Described alkali is triethylamine;

[0039] Propyl p-formamidobenzoate, POCl used in the reaction process 3 , the amount of alkali and organic solvent, according to propyl p-formamidobenzoate: POCl 3 : Alkali: organic solvent is calculated according to the ratio of 1mol: 1.5mol: 3mol: 4.17L;

[0040] (2), in the propyl p-isocyanobenzoate solution obtained in step (1), add 0.35g diethylamine and 0.08g Cu 2 0, the temperature was controlled at 70°C for 24 hours of reaction, after the obtained reaction solution was allowed to stand for stratification, the oil layer was taken, the resulting water layer was extracted with ethyl acetate, the oil layer w...

Embodiment 3

[0043] (1) Add 0.5g of propyl 4-formylaminobenzoate to a 25mL round bottom flask, add 10mL of organic solvent, then add 2.4g of alkali, stir, and drop in 0.74g of POCl3 , control the temperature to 70°C, and react for 2 hours to obtain a propyl p-isocyanobenzoate solution;

[0044] Described organic solvent is xylene;

[0045] Described alkali is triethylamine;

[0046] Propyl p-formamidobenzoate, POCl used in the reaction process 3 , the amount of alkali and organic solvent, according to propyl p-formamidobenzoate: POCl 3 : Alkali: organic solvent is calculated according to the ratio of 1mol: 2mol: 10mol: 4.17L;

[0047] (2), in the propyl p-isocyanobenzoate solution obtained in step (1), add 0.53g diethylamine and 0.1g Cu 2 0, the temperature was controlled at 130°C for 2 hours of reaction. After the obtained reaction solution was allowed to stand for stratification, the oil layer was taken, the water layer was extracted with ethyl acetate, the oil layer was taken, and th...

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Abstract

The invention discloses a propyl p-diethylaminomethylene benzoate compound and a preparation method thereof. The structural formula of the propyl p-diethylaminomethylene benzoate compound is as follows: Its preparation method is to react propyl p-formamidobenzoate with POCl3 in an organic solvent under alkaline conditions at a controlled temperature of 50-90°C for 0.25-4 hours to obtain a propyl p-isocyanobenzoate solution , then add diethylamine and Cu2O, control the temperature at 70-130°C and carry out the reaction for 2-24h, after the obtained reaction solution is allowed to stand and separate into layers, take the oil layer, the obtained water layer is extracted with ethyl acetate, take the oil layer, and combine twice The obtained oil layer is rotary evaporated to remove ethyl acetate, and column chromatography is used to spin off the solvent to obtain the propyl-p-diethylaminomethyleneaminobenzoate compound with insecticidal and bactericidal effects. The reaction process of the preparation method is simple and the reaction conditions Mild, the yield reaches about 80%.

Description

technical field [0001] The invention relates to a propyl-p-diethylaminomethylenebenzoate compound and a preparation method thereof. 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. Dimeform, N-(4-chloro-o-tolyl)-N,N-dimethylformamidine, is a high-efficiency broad-spectrum organic nitrogen agricultural insecticide and acaricide, which is effective against organophosphorus, organochlorine and amino Formic ester insecticides are effective in resistant insects and are moderately toxic, but the carcinogenicity of its metabolite 4...

Claims

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Application Information

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IPC IPC(8): C07C257/12
Inventor 杜葩
Owner SHANGHAI INST OF TECH
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