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Synthesis method of imazethapyr

A synthesis method and imazethapyr technology, applied in organic chemistry and other directions, can solve the problems of high requirements for instruments and conditions, high three wastes, and high costs, and achieve the effects of low equipment requirements, good reaction selectivity, and short reaction time.

Inactive Publication Date: 2020-12-29
SHANDONG RUNBO BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Phosphoric acid, ammonium hydroxide and other substances used in this method will cause the three wastes to be too high to be treated; it also requires a low temperature of minus 70°C, which requires too much equipment and conditions, resulting in high costs, so this solution has great potential. insufficient

Method used

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  • Synthesis method of imazethapyr
  • Synthesis method of imazethapyr
  • Synthesis method of imazethapyr

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Under the protection of nitrogen, according to the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid: acetic anhydride = 1:1.1, add to toluene, wherein toluene is the mass of 5-ethylpyridine-2,3-dicarboxylic acid 5 times of that, the reaction temperature is 35°C, HPLC detects after 1hr that after the reaction is over, add quantitative methanol, the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid:methanol=1:1.1, and the reaction temperature is 5 ℃, after 0.5hr, HPLC detects that the reaction is over, and solid sodium methoxide and 2-amino-2,3-dimethylbutyramide are added, and the molar ratio is 5-ethylpyridine-2,3-dicarboxylic acid: 2-amino- 2,3-Dimethylbutyramide:sodium methoxide=1:1.1:3. The temperature was raised to 110°C. After 1 hr, HPLC detected that the reaction was complete. The reaction solution was cooled to room temperature and an equal volume of water was added for extraction. Take the water phase and use dilute sulfuric acid with a mass fraction o...

Embodiment 2

[0034] Under the protection of nitrogen, according to the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid: acetic anhydride = 1:1.1, add to toluene, wherein toluene is the mass of 5-ethylpyridine-2,3-dicarboxylic acid 5 times of that, the reaction temperature is 30°C, and after 1hr, HPLC detects that after the reaction is completed, a quantitative amount of ethanol is added, the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid:ethanol=1:1.3, and the reaction temperature is - 5°C, after 0.5hr, HPLC detects that the reaction is over, add solid sodium ethoxide and 2-amino-2,3-dimethylbutyramide, the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid: 2-amino -2,3-Dimethylbutyramide: sodium ethoxide = 1:1.1:3. The temperature was raised to 110°C. After 1 hr, HPLC detected that the reaction was complete. The reaction solution was cooled to room temperature and an equal volume of water was added for extraction. Take the water phase and use dilute sulfuric acid with a m...

Embodiment 3

[0037] Under the protection of nitrogen, according to the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid:acetic anhydride=1:1.1, add it to xylene, where xylene is 5-ethylpyridine-2,3-dicarboxylate 5 times the mass of the acid, and the reaction temperature is 40°C. After 1 hr, HPLC detects that after the reaction is over, a certain amount of ethanol is added, and the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid: ethanol = 1:1.1 The reaction temperature is -10°C, after 0.5hr, HPLC detects that the reaction is over, add solid sodium ethoxide and 2-amino-2,3-dimethylbutyramide, the molar ratio of 5-ethylpyridine-2,3-dicarboxylic acid: 2- Amino-2,3-dimethylbutanamide:sodium ethoxide=1:1.1:3.5. The temperature was raised to 120°C. After 1 hr, HPLC detected that the reaction was complete. The reaction solution was cooled to room temperature and an equal volume of water was added for extraction. Take the water phase and use dilute sulfuric acid with a mass fraction of...

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Abstract

The invention relates to a synthesis method of imazethapyr, wherein the synthesis method comprises the steps: by using 5-ethylpyridine-2,3-dicarboxylic acid as a raw material, reacting with acetic anhydride to generate 5-methylpyridine-2,3-dicarboxylic anhydride; and under a low-temperature condition, continuing to react with alcohol to generate a compound represented by a structural formula (I),carrying out ring closing reaction with 2-amino-2,3-dimethylbutyramide under an alkaline condition, extracting to regulate the pH value, and thus obtaining the imazapyr product. The method has the advantages that the method is high in route reaction speed, extremely high in product purity, high in yield, mild in reaction condition, free of isomers and few in three wastes, the synthesis process isextensive, the reaction condition is optimized, the equipment cost of the reaction is reduced, the produced product is easy to separate, and the production process is simplified. The structural formula (I) is described in the specification.

Description

technical field [0001] The invention relates to a synthesis method of imazethapyr, in particular to a method for preparing imazethapyr by using a novel imazethapyr intermediate, and belongs to the technical field of imazethapyr preparation. Background technique [0002] Imazethapyr, also known as imazethapyr, belongs to imidazolinone herbicides. It is a high-efficiency, low-toxicity, broad-spectrum soybean field herbicide developed by American cyanamide company in the 1980s. Its structure is as follows: [0003] [0004] The synthesis of imazethapyr currently has the following processes: [0005] Patent CN102453022 reports that 2-[(1-cyano-1,2-dimethylpropyl)-formamido]-5-ethyl nicotinic acid is hydrolyzed into amide to prepare imazethapyr. This route has a long reaction period. There are too many intermediate processes, more three wastes are produced, and the cost is high, so there are big deficiencies. [0006] Patent US4861887 reports that imazethapyr is prepared by ...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 孙国庆侯永生朱素娟王嵩宋健
Owner SHANDONG RUNBO BIOTECH CO LTD