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A method for synthesizing 2-halo-3-substituted hydrocarbylsulfonylpyridine and its intermediates by microwave method

A technology of hydrocarbylsulfonylpyridine and benzyl, which is applied in the field of microwave synthesis of 2-halo-3-substituted hydrocarbylsulfonylpyridine and its intermediates, which can solve the problems of low yield, difficult large-scale production, and many "three wastes", etc. problems, to achieve the effect of high product yield, less side reactions and simple operation

Inactive Publication Date: 2019-03-19
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] It can be seen that the existing sulfonylpyridine preparation methods generally have problems such as many "three wastes" and low yields, and are difficult to scale production; moreover, most of the existing sulfonylpyridine preparations are carried out in organic solvents. See the report that adopts microwave method to prepare sulfonyl pyridine compound

Method used

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  • A method for synthesizing 2-halo-3-substituted hydrocarbylsulfonylpyridine and its intermediates by microwave method
  • A method for synthesizing 2-halo-3-substituted hydrocarbylsulfonylpyridine and its intermediates by microwave method
  • A method for synthesizing 2-halo-3-substituted hydrocarbylsulfonylpyridine and its intermediates by microwave method

Examples

Experimental program
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Effect test

Embodiment 1

[0074] Example 1: Preparation of 2-methylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile

[0075] In a 500mL three-necked flask equipped with a thermometer, first add 59.6g (0.5mol) of methylcyanoethylsulfone and KHCO 3 5.0g, then add 62mL (0.5mol) of 3-dimethylaminoacrolein, mix well, put the prepared reactor into the microwave instrument, set the microwave radiation conditions, at a temperature of 60°C, a microwave power of 100W and a frequency of The reaction was performed under the condition of 915MHz. TLC detection (petroleum ether:dichloromethane 1:2 development, sublimation iodine color development) 3-dimethylaminoacrolein reacted completely, and the reaction time was 0.5h. Add sodium carbonate solution to adjust the pH=7-8, separate the layers, extract the aqueous layer with 100 mL of ethyl acetate x 3 times, combine the organic layers, dry overnight with molecular sieves, filter, and recover the solvent by distillation to obtain 97.3 g of a light yellow solid wit...

Embodiment 2

[0080] Example 2: Preparation of 2-ethylsulfonyl-5-(N,N-diethyl)amino-2,4-pentadienenitrile

[0081] In a 500mL three-necked flask equipped with a thermometer, first add 66.6g (0.5mol) of ethyl cyanoethylsulfone, 20mL of diethanolamine, and then add 124mL (1.0mol) of 3-diethylaminoacrolein, mix well, and prepare Put the reactor into a microwave instrument, set the microwave radiation conditions, and react under the conditions of 80°C temperature, 200W microwave power and 915MHz frequency, TLC detection (petroleum ether: methylene chloride 1:2, sublimation iodine Color development) The reaction of ethyl cyanoethyl sulfone is complete, and the reaction time is 0.5h. Add a 10% potassium hydroxide solution to adjust the pH to 7-8, separate the layers, extract the aqueous layer with 100 mL of propyl acetate x 3 times, combine the organic layers, evaporate the organic phase under reduced pressure to recover the propyl acetate, and obtain a shallow Yellow solid 115.7g, melting point...

Embodiment 3

[0082] Example 3: Preparation of 2-isopropylsulfonyl-5-(N,N-diethyl)amino-2,4-pentadienenitrile

[0083] In a 500mL three-necked flask equipped with a thermometer, first add 73mL (0.6mol) of isopropylcyanoethyl sulfone and 10mL of piperidine, then add 62mL (0.5mol) of 3-diethylaminoacrolein, mix well, and prepare Put the reactor into a microwave instrument, set the microwave radiation conditions, react under the conditions of temperature 120°C, microwave power 350W and frequency 2450MHz, TLC detection (petroleum ether: dichloromethane 1:2, sublimation iodine display Color) 3-diethylaminoacrolein reacted completely, the reaction time was 0.2h, adding potassium carbonate solution to adjust the pH=7-8, separating the layers, extracting the aqueous layer with 100mL of dichloromethane×3 times, combining the organic layers, adding anhydrous Na 2 SO 4 After drying and filtering, the organic phase was evaporated to dichloromethane and recovered to obtain 119.5 g of a light brown oil...

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Abstract

The invention discloses a method for synthesizing 2-halo-3-substited alkylsulfonyl pyridine and an intermediate compound thereof through a microwave method. The method comprises the following steps: adding substituted amino acraldehyde, a catalyst and substituent cyanoethyl sulfone into a reactor, reacting under microwave radiation, and tracking the reaction until the substituted amino acraldehyde or the substituent cyanoethyl sulfone reacts completely, thereby preparing the intermediate compound; adding halogen hydride into the reaction solution, further reacting, and tracking detection until the reaction is complete; and adding an alkaline solution into the reaction solution to regulate the pH value to 7-8, standing for stratification to obtain a water layer and an organic layer, extracting the water layer with organic solvent, then merging the organic layers, and refining to prepare the 2-halo-3-substited alkylsulfonyl pyridine. According to the invention, the method for synthesizing 2-halo-3-substited alkylsulfonyl pyridine has the advantages of greenness, environment friendliness, short reaction time, simple operation process and high product yield; and the product has favorable bactericidal activity.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for synthesizing 2-halogeno-3-substituted hydrocarbylsulfonylpyridine and its intermediate by microwave method. Background technique [0002] Traditional organic reactions are mostly carried out in organic solvents, and most solvents are flammable, explosive, toxic, and unfriendly to the environment. Organic reactions carried out under microwave radiation conditions have low energy consumption, short time, and side reactions. Less, easy to purify, high yield, etc., has become a new organic synthesis technology emerging in the late 1980s, and has been developed rapidly at present, such as the synthesis of quinoline derivatives catalyzed by ammonium acetate under the promotion of microwaves (Tian Guifen, Chemical Industry Intermediates, 2006-01), Copper-Catalyzed Microwave-Assisted Synthesis of Benzimidazole Derivatives (Ke Fang, Organic Chemistry, 2014-05), Copper-Catalyz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/71C07C317/48C07C315/04A01N43/40A01P3/00
CPCA01N43/40C07C315/04C07C317/48C07D213/71
Inventor 刘玉法孙琳毛霏霏沈运朋张慧
Owner SHANDONG NORMAL UNIV
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