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Synthesis method of 1,2,3-diazosulfide compound

A technology of benzothiadiazoles and synthesis methods, which is applied in the chemical field, can solve the problems of large environmental pollution and poor atom economy, and achieve the effects of high reaction efficiency, reduced synthesis cost, and mild reaction conditions

Inactive Publication Date: 2017-11-03
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has disadvantages such as poor atom economy and high environmental pollution.

Method used

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  • Synthesis method of 1,2,3-diazosulfide compound
  • Synthesis method of 1,2,3-diazosulfide compound
  • Synthesis method of 1,2,3-diazosulfide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of 1,2,3-benzothiadiazole:

[0046]

[0047] At room temperature (25° C.), the raw materials o-aminothiophenol (0.3 mmol, 1 equiv) and tert-butyl nitrite (0.45 mmol, 1.5 equiv) were added to the reaction vessel, and then the reaction solvent water (2 mL) was added, Stir the reaction at a reaction temperature of 25°C for 3 minutes. After the reaction, add ethyl acetate (10 mL) to dilute the reaction solution, transfer the diluted solution to a separatory funnel, extract with saturated brine, and separate the aqueous phase and the organic phase. phase, then extract the aqueous phase with ethyl acetate for 2 to 4 times, combine all the organic phases, then add anhydrous sodium sulfate (5g) to dry the combined organic phase, filter after 5min, and wash the filter cake with ethyl acetate (5mL×3 times), then concentrated under reduced pressure, and finally the concentrate was separated by column chromatography (with petroleum ether and ethyl acetate volume ratio ...

Embodiment 2

[0056] Synthesis of 6-methyl-1,2,3-benzothiadiazole:

[0057]

[0058] At room temperature (25°C), the raw materials 2-amino-5-methylthiophenol (0.3 mmol, 1 equiv) and tert-butyl nitrite (0.45 mmol, 1.5 equiv) were added to the reaction vessel, and then added to the reaction Solvent water (2mL), stirred and reacted at 25°C for 3min, after the reaction, dilute the reaction solution by adding ethyl acetate (10mL), transfer the diluted solution to a separatory funnel, and extract with saturated saline , separate the aqueous phase and the organic phase, then extract the aqueous phase with ethyl acetate for 2 to 4 times, combine all the organic phases, then add anhydrous sodium sulfate (5g) to dry the combined organic phase, filter after 5min, and filter The cake was washed with ethyl acetate (5 mL×3 times), then concentrated under reduced pressure, and finally the concentrate was separated by column chromatography (with petroleum ether and ethyl acetate volume ratio 3:1 as the ...

Embodiment 3

[0067] Synthesis of 4,6-dimethyl-1,2,3-benzothiadiazole:

[0068]

[0069] At room temperature (25° C.), the raw materials 2-amino-3,5-dimethylthiophenol (0.3 mmol, 1 equiv) and tert-butyl nitrite (0.45 mmol, 1.5 equiv) were added to the reaction vessel, and then Then add reaction solvent water (2mL), and stir the reaction at 25°C for 3min. After the reaction, add ethyl acetate (10mL) to dilute the reaction solution, transfer the diluted solution to a separatory funnel, and use saturated Extract with salt water, separate the water phase and the organic phase, then extract the water phase with ethyl acetate 2 to 4 times, combine all the organic phases, then add anhydrous sodium sulfate (5g) to dry the combined organic phase, after 5min Filtration, the filter cake was washed with ethyl acetate (5 mL × 3 times), then concentrated under reduced pressure, and finally the concentrate was separated by column chromatography (with petroleum ether and ethyl acetate volume ratio 3:1 a...

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Abstract

The invention discloses a synthesis method of a 1,2,3-diazosulfide compound. A o-aminothiophenol compound with a structure shown as a formula (I) and tert-butyl nitrite are taken as raw materials, and are subjected to intramolecular diazo-reaction to obtain the 1,2,3-diazosulfide compound with a structure shown as a formula (II); a reaction equation is as follows (shown in the description), wherein R=hydrogen, fluorine, chlorine, ester group, nitro or methyl. The synthesis method has the beneficial effects that (1) the operation is simple and convenient in a preparation process, an obtained product is easy for after-treatment, and large-scale industrialized production is suitable; (2) reaction conditions are mild; (3) the synthesis cost is lowered; (4) a reaction substrate is high in functional group tolerance, is wide in range and easy to prepare; (5) the reaction is efficient, the yield is high, and the reaction efficiency is higher after reaction amplification; (6) environment pollution is avoided, and environment friendliness is achieved.

Description

technical field [0001] The invention relates to a synthesis method of a class of organic compounds, in particular to a synthesis method of 1,2,3-benzothiadiazole compounds, and belongs to the field of chemical technology. Background technique [0002] 1,2,3-Benzothiadiazole compounds are a class of nitrogen- and sulfur-containing heterocyclic compounds, which have biological activities such as sterilization, anti-inflammation, and inhibition of disordered growth of viruses, so they are widely used in organic synthesis intermediates, In dyes, preservatives, and often in the dominant structure of kinase inhibitors, especially in the field of medicinal chemistry, in order to improve or change the pharmacological activity, 1,2,3-benzene is often introduced into the structural modification of lead compounds or candidate drugs Thiadiazole compounds, for example: carboxylic acid compounds containing thiadiazole ring system, have the obvious function of inducing plant system to acqu...

Claims

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Application Information

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IPC IPC(8): C07D285/14
CPCC07D285/14
Inventor 刘妙昌刘玮张鑫高文霞黄小波吴华悦
Owner WENZHOU UNIVERSITY
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