Method for preparing 2-cyano-3-amino acrylic ester derivates

A technology of amino acrylate and derivatives, which is applied in the field of pesticides, can solve the problems of high toxicity and three wastes, and achieve the effect of no high temperature and high pressure, less three wastes, and simple production process

Active Publication Date: 2009-04-29
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0029] There are many steps in this method, and phosphorus oxychloride is used in the reaction, which has high toxicity and many wastes

Method used

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  • Method for preparing 2-cyano-3-amino acrylic ester derivates
  • Method for preparing 2-cyano-3-amino acrylic ester derivates
  • Method for preparing 2-cyano-3-amino acrylic ester derivates

Examples

Experimental program
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Effect test

Embodiment 1

[0051]Embodiment 1. In a 1000ml four-necked reaction flask with stirring, a thermometer and a condenser tube, drop into 206 grams of benzonitrile, 184 grams of ethanol, and 300ml of toluene, and control the reaction temperature at 5 to 10°C. Add about 140 grams of hydrogen chloride gas, and stir at room temperature for 15 to 16 hours after passing through, then remove excess hydrogen chloride gas under negative pressure, then add 200 ml of ethanol, and add excess triethylamine at room temperature to control the pH of the reaction solution At about 8, then heat up to reflux, add 220 g of ethyl cyanoacetate dropwise within 2 hours, continue to reflux for 5 to 6 hours, slowly cool to room temperature, cool to 0 to 5°C with an ice bath, keep for 1 hour, and dissolve the solid Filter out to obtain 395 grams of product with a content of 97% and a yield of 88.3%. ( 1 HNMR, (CDCl 3 d) 1.36(t, J=7.2Hz, 3H), 4.28(q, J=J=7.2Hz, 2H), 6.01(S, 1H), 7.44-7.58(m5H), 9.38(S, 1H)

Embodiment 2

[0052] Embodiment 2, similar to Example 1, only the hydrochloride of the obtained imino ether is filtered out, 220 grams of ethyl cyanoacetate is dissolved in the reaction bottle of 300ml ethanol, and the temperature in the reaction bottle is controlled at 5~ 10°C, add the filtered imino ether hydrochloride, then add an appropriate amount of triethylamine dropwise at this temperature, adjust the pH value of the reaction solution to 8-9, then heat up and reflux for 5-6 hours , slowly cooled to room temperature, cooled to 0-5°C with an ice bath, kept for 1 hour, and filtered off the solid to obtain 397 g of the product, with a content of 97.3% and a yield of 89.0%. The melting point is 122-124°C.

Embodiment 3

[0053] Embodiment 3, similar to Example 1, when allocating the imino ether pH, first add 100ml water, then add calcium carbonate in batches, when the recorded pH is about 5, use 30% potassium carbonate solution instead to control the pH of the reaction solution at 8 or so, the water layer was separated, dried with anhydrous sodium sulfate, and then the oil layer was returned to the reaction bottle, and the rest of the operations were the same to obtain 390.5 g of the product, with a content of 95.3%. , yield 85.3%. The melting point is 122-124°C.

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Abstract

The invention discloses a method for preparing a 2-cyano-3-amino acrylic ester derivative, which comprises the following steps: a compound (I) is taken as a raw material and reacts with C1 to C6 of fatty alcohols in an organic solvent in the presence of dry chlorine hydride to generate hydrochloride (II) of iminoether; and the obtained hydrochloride (II) of the iminoether or the filtered hydrochloride (II) of the iminoether reacts with cyanoacetate in the organic solvent in the presence of alkali to obtain the 2-cyano-3-amino acrylic ester derivative (III). The method for preparing the 2-cyano-3-amino acrylic ester derivative simplifies production process and has less three wastes; and the obtained product has high purity and high yield.

Description

technical field [0001] The invention belongs to the field of pesticides and relates to a preparation method of 2-cyano-3-aminoacrylate derivatives. Background technique [0002] Bioactive acrylic acid derivatives are currently one of the goals of new pesticide development and research, and have considerable scalability and structural modification potential. Among them, 2-cyano-3-aminoacrylate derivatives are used as pesticide fungicides. , to a large extent still belong to a class of compounds that have yet to be explored and have rich room for expansion and imagination. [0003] The original synthesis of the target compound 2-cyano-3-aminoacrylate derivatives is mainly achieved through the following approaches, and there are mainly the following six types reported in the literature. [0004] Method 1 (J.Am.Chem.Soc..1943, 40, 388~390): [0005] It is prepared by condensation of amidine and cyanoacetate. The reaction between cyanoacetate and amidine generates two products,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/30C07C253/30
Inventor 王宁曹燕蕾谢欣王达张磊朱晶曹庆亮徐巍
Owner JIANGSU PESTICIDE RES INST
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