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Preparation method of thiazole methylamino pyridine compound

A technology for thiazolemethanylaminopyridines and compounds, which is applied in the field of preparation of thiazolylmethanylaminopyridines, can solve the problems of unsuitable industrial production, large amount of potassium carbonate, and troublesome recycling, and achieve easy recycling and reduced production costs , Improve the effect of reaction speed

Active Publication Date: 2015-03-04
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

DMF is used as a solvent for the reaction, and a large amount of water needs to be added for post-treatment. DMF and water are mixed, and industrial recovery is difficult, and the amount of potassium carbonate is also large. Recovery is troublesome, time-consuming, energy-consuming, and the amount of three wastes is large. The cost is high and it is not suitable. Industrial production

Method used

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  • Preparation method of thiazole methylamino pyridine compound
  • Preparation method of thiazole methylamino pyridine compound
  • Preparation method of thiazole methylamino pyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 2-chloro-5-ethylaminomethylthiazole 185.2g (95%, 1.0mol), 2-chloro-6- 203.5g (97%, 1.05mol) of methoxy-3-nitropyridine, 1500ml of toluene, and 3.23g (0.01mol) of catalyst tetrabutylammonium bromide, started stirring, and added dropwise at 10-20°C with a mass fraction of 200.1 g (1.5 mol) of 30% aqueous sodium hydroxide solution was added after dropping, heated to raise the temperature, and the temperature was controlled at 30° C. for 2 hours. After the reaction was completed, cool to room temperature, separate layers, adjust the oil layer to neutrality with 10% dilute hydrochloric acid, wash twice with 500ml water, separate layers, and desolvate the oil layer under reduced pressure to obtain 291.9 g of a dark yellow crude product, which was recrystallized, filtered, and dried. After drying, 277.4 g of a light yellow solid product was obtained, with a yield of 83.3%, and a gas chromatography quantitative analysis content of 98.5%. 1 H NMR (CDCl 3 / TMS,300MHz)δ(ppm)...

Embodiment 2

[0020] Add 2-chloro-5-ethylaminomethylthiazole 185.2g (95%, 1.0mol), 2-chloro-6- Methoxy-3-nitropyridine 203.5g (97%, 1.05mol), toluene 1500ml, catalyst benzyltrimethylammonium chloride 1.87g (0.01mol), start stirring, drop the mass at 10~20℃ 200.1 g (1.5, mol) of sodium hydroxide aqueous solution with a fraction of 30% was added, and the temperature was raised after dropping, and the temperature was controlled at 30° C. for 2 hours. After completion of the reaction, cool to room temperature, separate layers, adjust the oil layer to neutral with an appropriate amount of 10% dilute hydrochloric acid, wash twice with 500ml water, separate layers, and desolvate the oil layer under reduced pressure to obtain 290.1 ​​g of a dark yellow crude product, which is recrystallized, filtered, After drying, 275.0 g of a light yellow solid product was obtained, with a yield of 82.5%, and a gas chromatography quantitative analysis content of 98.4%.

Embodiment 3

[0022] Add 185.2 g (95%, 1.0 mol) of 2-chloro-5-ethylaminomethylthiazole, 2-chloro-6- Methoxy-3-nitropyridine 203.5g (97%, 1.05mol), toluene 1500ml, catalyst benzyltriethylammonium chloride 2.28g (0.01mol), start stirring, drop the mass at 10~20℃ 200.1 g (1.5 mol) of a 30% aqueous sodium hydroxide solution was added, after the droplet was completed, the temperature was raised, and the temperature was controlled at 30° C. for 2 hours. After the reaction was completed, cool to room temperature, separate layers, adjust the oil layer to neutral with an appropriate amount of 10% dilute hydrochloric acid, then wash twice with 500ml water, separate layers, and desolvate the oil layer under reduced pressure to obtain 292.3 g of a dark yellow crude product, which was recrystallized, filtered, After drying, 280.2 g of a light yellow solid product was obtained, with a yield of 83.9%, and a gas chromatography quantitative analysis content of 98.2%.

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Abstract

The invention discloses a method for synthesizing a thiazole methylamino pyridine compound 6-methoxy-N-((2-chlorothiazol-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine. According to the method, 2-chloro-5-ethylaminemethylthiazol and 2-chloro-6-methoxy-3-nitropyridine are used as raw materials; toluene is adopted as a solvent; a sodium hydroxide water solution is used as an acid-binding agent; and the synthesis is carried out under the effect of a catalyst tetrabutyl ammonium bromide, or benzyltrimethyl ammonium chloride, or benzyltriethyl ammonium chloride, or tetraethyl ammonium bromide, or tetrabutyl ammonium iodide. A chemical reaction formula is shown below. According to the invention, the acid-binding agent and the reaction solvent are changed, and the catalyst is added, such that reaction is full and complete, reaction speed is greatly improved, reaction time is shortened, reaction yield is improved, and product purity is improved. The process is simple to operate. Post-treatments of the novel solvent toluene and the acid-binding agent sodium hydroxide water solution are simple, and the solvent and the acid-binding agent are easy to recycle. With the method, three-waste amount is low, production cost is reduced, and industrialized application value is high.

Description

technical field [0001] The present invention relates to a preparation method of thiazolemethanylpyridine compounds, especially thiazolemethanylpyridine compound 6-methoxy-N-((2-chlorothiazol-5-yl)methyl)-N- Preparation method of ethyl-3-nitropyridin-2-amine. Background technique [0002] 6-Methoxy-N-((2-chlorothiazol-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine is a new fungicide independently designed and synthesized by Hunan Research Institute of Chemical Industry . It exhibits excellent activity against Sclerotinia sclerotiorum, Cucumber Botrytis, Tobacco Alternaria, Cotton Fusarium wilt, Apple Leaf Spot, etc. It can be used in agriculture, horticulture, flower disease control, and has low toxicity to humans and animals. Its similar compound has been authorized by the Chinese invention patent (patent authorization number is ZL 201110443914.1), and its structural formula is: [0003] [0004] The preparation method of the patent disclosed 6-methoxy-N-((2-chlorothiazol...

Claims

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Application Information

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IPC IPC(8): C07D417/12
CPCC07D417/12
Inventor 杜升华刘卫东兰世林刘源胡志彬王艳丽
Owner 湖南海利常德农药化工有限公司
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