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Synthesis method of 2-pyrazine carboxylic ester compound

The technology of an ester compound and a synthesis method is applied in the synthesis field of 2-pyrazine carboxylate compound, can solve the problems of complicated reaction process and high cost, and achieves the effects of simple operation, mild reaction conditions and wide source of raw materials

Active Publication Date: 2021-04-13
江苏广域化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The main purpose of the present invention is to provide a kind of synthetic method of 2-pyrazinecarboxylate compound, to solve the complicated reaction process that the synthetic method of 3-trifluoromethyl-2-pyrazinecarboxylic acid methyl ester exists in the prior art , the problem of high cost

Method used

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  • Synthesis method of 2-pyrazine carboxylic ester compound
  • Synthesis method of 2-pyrazine carboxylic ester compound
  • Synthesis method of 2-pyrazine carboxylic ester compound

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preparation example Construction

[0021] In a typical embodiment of the present application, a synthetic method of 2-pyrazinecarboxylate compounds is provided, the synthetic method comprising: step S1, compound 1 and glyoxal dioxime in a Lewis acid catalyst Under the action of addition reaction, intermediate 1 is obtained; step S2, intermediate 1 undergoes the first dehydration reaction to obtain 2-pyrazinecarboxylate compounds, wherein, compound 1, intermediate 1, 2-pyrazinecarboxylate The general structural formula of ester compounds is as follows:

[0022] R 1 for C 1 ~C 15 Substituted or unsubstituted alkyl, R 2 for C 1 ~C 10 of alkyl.

[0023] The preparation cost (or commercial price) of the starting material compound 1 that the present invention adopts is generally far lower than trifluoropyruvate methyl ester compound; The carbon-nitrogen double bond is added to reduce the probability of self-polymerization of compound 1 as much as possible, so as to obtain a ring-forming intermediate, and the...

Embodiment 1

[0039] Step 1: Restore

[0040]

[0041] First, add 150mL of tetrahydrofuran and 20.9g (0.387mol) of potassium borohydride to a 500mL glass three-neck flask, under nitrogen protection, stir and raise the temperature to 40-45°C, control the temperature between 40-45°C, drop Add 50g (0.352mol) of a mixture of methyl trifluoroacetoacetate and 50mL of tetrahydrofuran, and finish adding in about 1 hour. After the addition, raise the temperature to 60-65°C, continue to keep warm for 4 hours, take samples, and after the central control is qualified, Cool down to 20-25°C and wait for hydrolysis; in another 1000mL reaction bottle, add 209g of water and 91g of 31% hydrochloric acid (0.774mol), replace with nitrogen 3-5 times, and stir to cool down to 0-10°C. Slowly add the aforementioned reaction liquid into hydrochloric acid water for hydrolysis; while adding, continue to stir and lower the temperature, and control the adding speed so that the hydrolysis temperature is kept between ...

Embodiment 2

[0055] The difference between Example 2 and Example 1 is that the catalyst for the fourth step reaction is 0.80 g of zinc chloride, and the temperature of the addition reaction is 90° C. to finally obtain methyl 3-trifluoromethyl-2-pyrazinecarboxylate .

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Abstract

The invention provides a synthetic method of a 2-pyrazine carboxylic ester compound. The synthesis method comprises the following steps: S1, carrying out addition reaction on a compound 1 and glyoxal dioxime under the action of a Lewis acid catalyst to obtain an intermediate 1; and step S2, carrying out first dehydration reaction on the intermediate 1 to obtain the 2-pyrazine carboxylic ester compound, wherein the structural general formulas of the compound 1, the intermediate 1 and the 2-pyrazine carboxylic ester compound are sequentially shown in the specification, R1 being a C1-C15 substituted or unsubstituted alkyl group, and R2 being a C1-C10 alkyl group. The preparation cost (or commercially available price) of the initial raw material compound 1 adopted by the invention is generally far lower than that of a trifluoropyruvate methyl ester compound. Compared with the traditional preparation method of 3-trifluoromethyl-2-methyl pyrazinecarboxylate, the method has the advantages of mild reaction conditions, simple operation and wide raw material sources, avoids the use of an expensive coupling catalyst, and greatly reduces the cost.

Description

technical field [0001] The invention relates to the technical field of synthesis of 3-trifluoromethyl-2-pyrazinecarboxylic acid methyl ester, in particular to a synthesis method of 2-pyrazinecarboxylic acid ester compounds. Background technique [0002] Methyl 3-trifluoromethyl-2-pyrazinecarboxylate (compound 1A) is a compound with fungicidal activity. After compound 1A is prepared into a pyrazine carboxamide derivative or its salt, it can be used as a fungicide for agriculture and gardening, and thus 3-trifluoromethyl-2-pyrazinecarboxylic acid methyl ester is prepared into a broad-spectrum insecticide in the synthesis of pesticides Has a wider range of applications. Its most commonly used preparation method is shown in reaction 1-1: [0003] [0004] In the above method, methyl trifluoropyruvate is used as a starting material, and compound 1A is obtained through ring closure, dehydrogenation, chlorination, and esterification of methyl pyruvate and ethylenediamine. The...

Claims

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Application Information

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IPC IPC(8): C07D241/24
CPCC07D241/24
Inventor 康杰徐磊何乐
Owner 江苏广域化学有限公司
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