Method for synthesizing 2-hylogen-3-alkyl substituted sulfonyl pyridine and midbody thereof in ultrasonic method

A technology of hydrocarbyl sulfonyl pyridine and hydrocarbyl sulfonyl, which is applied in the field of ultrasonic synthesis of 2-halogenated-3-substituted hydrocarbyl sulfonyl pyridine and its intermediates, and can solve the problem of intractability, low yield, and many "three wastes", etc. question

Inactive Publication Date: 2017-05-31
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The disadvantage of this method is that the reaction time is long, the three wastes are more, it is difficult to handle, and the yield is low, and the yield is 64%.
[0015] It can be seen that the existing 2-halogenated-3-ethylsulfonylpyridine preparation meth

Method used

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  • Method for synthesizing 2-hylogen-3-alkyl substituted sulfonyl pyridine and midbody thereof in ultrasonic method
  • Method for synthesizing 2-hylogen-3-alkyl substituted sulfonyl pyridine and midbody thereof in ultrasonic method
  • Method for synthesizing 2-hylogen-3-alkyl substituted sulfonyl pyridine and midbody thereof in ultrasonic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Preparation of 2-methylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile

[0056] In a 500mL three-neck round bottom flask, add 62mL (0.5mol) of 3-dimethylaminoacrolein, 10mL of triethylamine and 59.6g (0.5mol) of methylcyanoethylsulfone, mix well, and prepare the reaction Put the device into the ultrasonic instrument, set the ultrasonic radiation conditions, react under the conditions of temperature 120°C, ultrasonic power 350W and frequency 100KHz, high performance liquid phase tracking and detection of the reaction process until the end of the reaction, add 10mL of deionized water to remove impurities, The crude product was obtained by filtration, and then recrystallized with absolute ethanol to obtain 96.8 g of a light yellow solid with a melting point of 169-171° C. and a product yield of 96.7%. After HR-MS, 1 H NMR, 13 According to CNMR spectrum, the product is 2-methylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile.

[0057] HR-MS of the prod...

Embodiment 2

[0067] Example 2 Preparation of 2-ethylsulfonyl-5-(N,N-diethyl)amino-2,4-pentadienenitrile

[0068] In a 500mL three-necked round-bottomed flask, add 124mL (1.0mol) of 3-diethylaminoacrolein, 10mL of sodium ethoxide and 66.6g (0.5mol) of ethyl cyanoethyl sulfone, mix well, and place the prepared reactor Put it into the ultrasonic instrument, set the ultrasonic radiation conditions, react under the conditions of temperature of 100°C, ultrasonic power of 300W and frequency of 80KHz, TLC detection (petroleum ether: methylene chloride 1:3, sublimation iodine color development) B The reaction of cyanoethyl sulfone was complete, 10 mL of deionized water was added to remove impurities, and the organic phase was distilled to remove the solvent to obtain 116.2 g of a light yellow solid with a melting point of 155-157°C and a yield of 95.9%. The product was characterized by HR-MS, that is, 2-ethylsulfonyl-5-(N,N-diethyl)amino-2,4-pentadienenitrile. HR-MS(ESI):m / zCalcd for C 11 h 18 N...

Embodiment 3

[0069] Example 3 Preparation of 2-isopropylsulfonyl-5-(N,N-diethyl)amino-2,4-pentadienenitrile

[0070] In a 500mL three-neck round bottom flask, add 50mL (0.4mol) of 3-diethylaminoacrolein, 10mL of sodium isopropoxide and 66.6g (0.5mol) of isopropylcyanoethyl sulfone, mix well, and prepare Put the reactor into the ultrasonic instrument, set the ultrasonic radiation conditions, react under the conditions of temperature 80°C, ultrasonic power 300W and frequency 80KHz, TLC detection (petroleum ether: dichloromethane 1:2, sublimation iodine display Color) 3-diethylaminoacrolein was completely reacted, 10 mL of deionized water was added to remove impurities, and the organic phase was distilled to remove the solvent to obtain 97.5 g of light brown oil with a yield of 95.1%. The product was characterized by HR-MS, that is, 2-isopropylsulfonyl-5-(N,N-diethyl)amino-2,4-pentadienenitrile. HR-MS(ESI):m / z Calcd for C 12 h 20 N 2 o 2 S 279.3542[M+Na] + ,found 279.3520[M+Na] + .

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Abstract

The invention discloses a method for synthesizing 2-hylogen-3-alkyl substituted sulfonyl pyridine and midbody thereof in an ultrasonic method. The method comprises the following steps: enabling substituted amino acraldehyde, a catalyst and substituted cyanoethyl sulfone to react under ultrasonic until the complete reaction to prepare a reaction solution of a 2-hylogen-3-alkyl substituted sulfonyl pyridine midbody; adding halogen hydride into the reaction solution at a certain of temperature, facilitating the continuous reaction until the complete reaction, adding an alkaline solution into the reaction solution, adjusting a pH value to 7 to 8, standing, layering into a water layer and an organic layer, extracting the water layer by using an organic solvent, combining the organic layer, refining to obtain the 2-hylogen-3-alkyl substituted sulfonyl pyridine. The 2-hylogen-3-alkyl substituted sulfonyl pyridine is synthesized by adopting the ultrasonic method, so that the organic synthetic reaction can be effectively facilitated, the reaction speed is increased, the reaction yield is increased, and the environmental protection is facilitated; and the reaction time is short, the operation is simple, the reaction can be completed generally in two hours, the product yield is high, the quality is good, and the yield can reach 90 percent or more which is higher than the yield of the traditional solvent-method heating refluxing method.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for synthesizing 2-halogenated-3-substituted alkylsulfonylpyridine and its intermediate by an ultrasonic method. Background technique [0002] In organic synthesis, usually the chemical reaction takes several hours or tens of hours, consumes a large amount of organic solvent, consumes a lot of energy, and has low efficiency. The application of ultrasonic technology in organic synthesis can not only improve the reaction conditions, but also speed up the reaction speed. And improve the reaction yield, and even change the reaction path of some reactions, so that some reactions that are difficult to carry out under traditional conditions can be realized, which has outstanding advantages. [0003] Pyridine and its derivatives are an important class of nitrogen-containing heterocyclic compounds, which have the advantages of high biological activity, good ...

Claims

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Application Information

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IPC IPC(8): C07D213/71C07C317/48C07C315/04A01P3/00
CPCC07C315/04C07D213/71C07C317/48
Inventor 刘玉法张彦春孙南毛霏霏薄文正
Owner SHANDONG NORMAL UNIV
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