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New synthesis method of benzothiacyclopentadiene

A benzothiolene, a newly synthesized technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, high reaction temperature, low yield, etc., to improve product yield and content, and mild reaction conditions , The effect of high product yield

Inactive Publication Date: 2020-07-17
宁波海曙琼杰化工技术研发工作室
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are not many reports on the methods of synthesizing benzothiolene at home and abroad, and most of them are difficult to realize industrial production. Benzothiole can be synthesized from hydrogen sulfide and styrene under the same conditions, and the conversion rate is 60%. This method can synthesize the target product, but the reaction conditions are harsh and it is not easy for industrialization
CN103717587A provides a method for synthesizing substituted benzothiolene by substituted benzaldehyde and methyl thioglycolate as raw materials, but there are disadvantages of high reaction temperature during cyclization and difficult post-treatment, making it difficult to industrialize
CN105294785A discloses C-benzo five-membered heteroaromatic ring-like aryl glucoside derivatives and its preparation method and application, which provides a method for synthesizing benzothiolene from thiophenol and bromoacetaldehyde diethyl acetal method, bromoacetaldehyde diethyl acetal is expensive, and the method yield is low, unsuitable for industrialized production

Method used

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  • New synthesis method of benzothiacyclopentadiene
  • New synthesis method of benzothiacyclopentadiene
  • New synthesis method of benzothiacyclopentadiene

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Synthesis of Benzothiole

[0036] (1) Add 400ml of xylene and 320g of sodium bicarbonate to a 2L four-neck flask, start stirring, start to add 1250g of 10% chloroacetaldehyde dropwise, control the material temperature at 20-25°C with cooling water, take 60 minutes, drop After the addition is complete, stir for 20 minutes, add 150 g of thiophenol into the reaction bottle, after the addition is complete, raise the temperature to 60-65 ° C, keep the temperature constant for 5 hours, after the reaction is completed, separate layers, take the upper organic layer as the intermediate layer, and use it in the next step synthesis;

[0037] (2) Add 800ml of xylene and 50g of polyphosphoric acid to a 2L four-neck flask, stir and raise the temperature to 80°C, add 80g of phosphorus pentoxide, then raise the temperature to 120-125°C, and start to slowly add the step intermediate, At the same time, the temperature of the kettle was controlled at 120-125°C for 5 hours. After the addi...

Embodiment 2

[0039] Synthesis of Benzothiole

[0040] (1) Add 400ml of toluene and 260g of potassium carbonate to a 2L four-neck flask, start stirring, start to add 1250g of 10% chloroacetaldehyde dropwise, use cooling water to control the temperature of the material at 20-25°C, take 60 minutes, and complete the dropwise addition , stirred for 20 minutes, added 150 g of thiophenol into the reaction bottle, after the addition was completed, the temperature was raised to 60-65 ° C, and the temperature was kept constant for 5 hours. After the reaction was completed, the layers were separated, and the upper organic layer was taken as the intermediate layer for the next step of synthesis;

[0041] (2) Add 800ml of toluene and 50g of polyphosphoric acid into a 2L four-neck flask, stir and heat up to 80°C, add 80g of phosphorus pentoxide, then raise the temperature to 120-125°C, and start to slowly add the intermediates dropwise, at the same time Control the temperature of the kettle at 120-125°C...

Embodiment 3

[0043] Synthesis of 5-Chlorobenzothiolene

[0044] (1) Add 200ml of ethylbenzene and 160g of sodium bicarbonate to a 1L four-necked flask, start stirring, start to add 625g of 10% chloroacetaldehyde dropwise, control the temperature of the material at 20-25°C with cooling water, take 40 minutes, drop After the addition is completed, stir for 20 minutes, add 100 g of 4-chlorothiophenol into the reaction bottle, after the addition is completed, heat up to 65-70 ° C, keep the temperature constant for 4 hours, after the reaction is completed, separate layers, take the upper organic layer as the intermediate layer, and use synthesized in the next step;

[0045] (2) Add 600ml of ethylbenzene and 50g of polyphosphoric acid to a 2L four-necked flask, stir and raise the temperature to 80°C, add 50g of phosphorus pentoxide, then raise the temperature to 125-130°C, and start adding the step intermediate slowly, At the same time, the temperature of the kettle was controlled at 125-130°C ...

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Abstract

The invention discloses a novel synthesis method of benzothiacyclopentadiene, and belongs to the technical field of synthesis. The method comprises the following steps that: under an alkaline condition, chloroacetaldehyde and thiophenol undergo a Williamson condensation reaction to obtain thiophenyl acetaldehyde, the thiophenyl acetaldehyde undergoes a cyclization and dehydration reaction with a dehydrating agent under an acidic condition, water is added, layering is performed, an organic layer is taken, and reduced pressure distillation is performed to obtain the target product benzothiacyclopentadiene. The method has the advantages of simple operation, mild reaction, easy realization of industrialization, and high product yield.

Description

technical field [0001] The invention relates to a new synthesis method of benzothiolene, which belongs to the technical field of organic synthesis. Background technique [0002] This patent relates to the field of medicinal chemistry, and provides a synthesis method of benzothiolene and substituted benzothiolene compounds. [0003] At present, there are not many reports on the methods of synthesizing benzothiolene at home and abroad, and most of them are difficult to realize industrial production. Benzothiole can be synthesized by hydrogen sulfide and styrene under certain conditions, and the conversion rate is 60%. This method can synthesize the target product, but the reaction conditions are harsh and it is not easy for industrialization. CN103717587A provides a method for synthesizing a substituted benzothiolene from substituted benzaldehyde and methyl thioglycolate as raw materials, but it has the disadvantages of high reaction temperature during cyclization and difficu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/54
CPCC07D333/54
Inventor 刘碧见
Owner 宁波海曙琼杰化工技术研发工作室
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