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Synthesis method of key intermediate of imidazolinone compound

A technology of imidazolinones and synthetic methods, which is applied in the field of pesticide chemistry, can solve problems such as many side reactions, high reaction temperature, and danger, and achieve the effects of improving yield and purity, reducing production costs, and short reaction steps

Pending Publication Date: 2022-06-21
JIANGSU FLAG CHEM IND
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] Chinese invention patent CN104447527A discloses a method for dialkyl pyridine-2,3-dicarboxylate, although the yield can be 82-96%, but it needs to use dangerous catalyst sodium amide, sodium hydrogen or triphenyl Sodium methyl is not conducive to industrial production. In addition, the reaction temperature is high, causing many side reactions, and it is difficult to control the reaction, and the process is complicated
[0008] Therefore, as an important intermediate in the synthesis of imidazolinone compounds, the existing synthetic methods of pyridine-2,3-dicarboxylates are not ideal enough, and there is an urgent need for a method with short reaction steps, easy-to-obtain raw materials, mild reaction, and high product yield. Synthetic method of pyridine-2,3-dicarboxylate with higher yield and purity Synthetic method

Method used

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  • Synthesis method of key intermediate of imidazolinone compound
  • Synthesis method of key intermediate of imidazolinone compound
  • Synthesis method of key intermediate of imidazolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of (E)-dimethyl 2-(dimethylaminomethylene)-3-oxosuccinate:

[0036]

[0037] 160.13g (1mol) dimethyl oxaloacetate and 119.16g (1mol) N,N-dimethylformamide dimethyl acetal were mixed and dissolved in dichloromethane, and the reaction was stirred at room temperature for 1h. After the reaction was completed, the mixture was evaporated under reduced pressure. The solvent was removed to obtain 213.05g of oil, the qualitative content was 98%, and the weight yield was 99%. 1 H NMR (400MHz, DMSO) δ 7.96(d, J=5.5Hz, 1H), 3.70(s, 3H), 3.59(s, 3H), 3.40(s, 3H), 2.94(s, 3H).

Embodiment 2

[0039] Preparation of methyl 5-methylpyridine-2,3 dicarboxylate:

[0040]

[0041] 213.05 g of (E)-dimethyl 2-(dimethylaminomethylene)-3-oxosuccinate (0.97 mol) with a purity of 98% and 143.93 g of ammonium sulfamate (1.26 mol) It was dissolved in 450g methanol, 0.98g concentrated sulfuric acid (0.01mol) was added, the temperature was raised to 50°C, and 61.98g propionaldehyde (1.07mol) was added dropwise into the reaction system. After the solvent was evaporated, water was added, the layers were extracted with dichloroethane, and the solvent was removed to obtain 192.81 g of a yellow solid with a qualitative content of 98% and a weight yield of 95%. 1 H NMR (400MHz, DMSO) δ 8.67–8.62 (m, 1H), 8.11 (dd, J=1.9, 0.7Hz, 1H), 3.85 (s, 6H), 2.41 (s, 3H).

Embodiment 3

[0043] Preparation of methyl 5-ethylpyridine-2,3 dicarboxylate:

[0044]

[0045]213.05 g of (E)-dimethyl 2-(dimethylaminomethylene)-3-oxosuccinate (0.97 mol) with a purity of 98% and 132.86 g of ammonium sulfamate (1.16 mol) Dissolve in 600g of ethanol, add 2.94g of concentrated sulfuric acid (0.03mol), heat up to reflux, add 73.25g of butyraldehyde (1.02mol) dropwise into the reaction system, dropwise for 2h, keep stirring for 3h after the addition is complete, and after the reaction tracking ends The solvent was evaporated, water was added, the layers were extracted with toluene, and the solvent was removed to obtain 184.69 g of a yellow solid with a qualitative content of 96% and a weight yield of 91%.

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Abstract

The invention relates to the field of pesticide chemistry, in particular to a synthesis method of an imidazolinone compound key intermediate, which comprises the following steps: dissolving a compound II and a compound III in an organic solvent, reacting while stirring, and evaporating to remove the solvent after the reaction to obtain an intermediate I; dissolving the intermediate I in an organic solvent, adding an ammonia source, a catalyst and a compound IV, and performing heat treatment reaction to obtain a compound V; the synthesis method of the key intermediate of the imidazolinone compound provided by the invention has the advantages of short reaction steps, easily available raw materials and mild reaction, improves the yield and purity of the product, reduces the production cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of pesticide chemistry, in particular to a method for synthesizing pyridine-2,3-dicarboxylate, a key intermediate of imidazolinone compounds. Background technique [0002] As high-efficiency herbicides, imidazolinones mainly inhibit the activity of acetate hydroxy acid synthases (AHAs) and affect the biosynthesis of three branched-chain amino acids—valine, leucine and isoleucine. Ultimately destroy protein synthesis, interfere with DNA synthesis and cell division and growth. Imazethapyr, imazethapyr and imazethapyr are important components of imidazolinone herbicides. [0003] US Patents US4948896A and US5047542A disclose methods for synthesizing pyridine-2,3-dicarboxylate through dialkyl maleate derivatives, but the yield is only 66-88%, and the purity is only 69-93%, The overall level is relatively low, and at the same time, there is also the problem of high organic wastes in the production process, which is diffi...

Claims

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Application Information

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IPC IPC(8): C07C227/10C07C229/30C07D213/80C07D213/803
CPCC07C227/10C07C229/30C07D213/80C07D213/803
Inventor 赵渭张璞黄瑞琦吴耀军
Owner JIANGSU FLAG CHEM IND
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