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Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile

A technology for synthesizing thiobenzamide and thiobenzamide, which is applied in the direction of organic chemistry and the like, can solve the problems of high reaction cost, many by-products in the reaction process, low conversion rate and the like, and achieves a simple reaction system and wide adaptability. , the effect of easy availability

Inactive Publication Date: 2019-01-15
INNER MONGOLIA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods usually require harsh conditions to make the reaction go smoothly, specifically as 1) the sulfur source is highly toxic; 2) the reaction cost is high; 3) the post-treatment is complicated; 4) the conversion rate is low; 5) the substrate applicability is poor ; 6) many by-products in the reaction process

Method used

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  • Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile
  • Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile
  • Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-15

[0037] Example 1-15: Synthesis of o-fluorobenzothiobenzamide with o-fluorobenzonitrile

[0038] Put a magnet into a 10mL stainless steel autoclave, and add 1mmol of o-fluorobenzonitrile, an appropriate amount of inorganic sulfide and 2ml of solvent in sequence, and tighten the autoclave. Fill the reactor with 0.1MPa of CO 2 , Stir the reaction for 2h, after the reaction is completed, slowly exhaust the gas in the reaction kettle, unscrew the reaction kettle, and transfer the solution in the reaction kettle to a 50mL Erlenmeyer flask. After adding saturated brine, it was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous magnesium sulfate for 30 minutes. Anhydrous magnesium sulfate was removed by filtration, and the crude product was obtained by distillation under reduced pressure. Use a mixed solvent of petroleum ether and ethyl acetate as eluent, separate and concentrate through column chromatography (200-300 mesh silica gel) to obta...

Embodiment 16～24

[0044] Examples 16-24: Synthesis of thiobenzamide derivatives.

[0045] The following thiobenzamide derivatives were synthesized with reference to the optimal conditions of o-fluorothiobenzamide.

[0046] Among them: the temperature is 25°C, the pressure is 0.1MPa, o-fluorobenzonitrile: inorganic sulfide = 1:2, the molar ratio of o-fluorobenzonitrile and carbon dioxide is 1:0.3; the solvent is DMF, the inorganic sulfide is NaHS, and the reaction time 24h.

[0047] The relevant data are listed in Table 2.

[0048]

[0049] Table 2: Synthesis of thiobenzamide derivatives

[0050]

[0051]

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Abstract

The invention discloses a method for synthesizing a thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile. The method comprises the following steps: taking the substituted benzonitrile as a raw material, an inorganic sulfide as a sulfur source and CO2 as an auxiliary agent for reacting in the presence of a reaction solvent, and concentrating and purifying a reaction solution to obtain the thiobenzamide derivative. The reaction system disclosed by the invention is relatively simple, other catalysts are not added outside a reactant and the inorganic sulfide, themethod is suitable for synthesis of high-additional-value thiobenzamide containing a plurality of substituent groups, the reaction is carried out at low temperature and low pressure, and the risk coefficient is reduced.

Description

technical field [0001] The invention relates to the technical field of polymer synthesis, and furthermore, relates to a method for synthesizing thiobenzamide derivatives by regulating and substituting benzonitrile with CO2. Background technique [0002] Thioamides are a class of important chemical structures with biological activity, and they are often used as intermediates with excellent properties. In medicine, it is used for the synthesis of drugs for treating diseases such as hyperthyroidism, tuberculosis and leprosy; in industry, it is used for the synthesis of structures such as thiazole, thiazoline and thiazolinone, and can also be used as a catalyst and a booster for rubber vulcanization agents or metal corrosion inhibitors, etc. Due to the wide application of thioamide derivatives, domestic and foreign efforts are being made to develop their synthetic methods. According to literature reports, oximes, nitriles, amides, haloacetylenes, carboxylic acids, primary amine...

Claims

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Application Information

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IPC IPC(8): C07C327/48
CPCC07C327/48
Inventor 竺宁桑国智李闪闪宋壮壮洪海龙闫丽岗韩利民
Owner INNER MONGOLIA UNIV OF TECH
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