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Aryl alkenyl thioether compound and preparation method thereof

A technique for aralkenyl thioether and compound, which is applied in the field of compound preparation, can solve the problems such as rare synthesis method of alkenyl thiocyanate, no synthesis method, etc., and achieves wide application range of substrates, simple operation and selectivity. Good results

Active Publication Date: 2020-10-30
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the preparation of sulfur-containing compounds is more about the synthesis of aryl and alkyl thiocyanates, and the synthesis of alkenyl thiocyanates is rare, especially the introduction of two compounds containing There is no corresponding synthetic method for the method of sulfur group

Method used

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  • Aryl alkenyl thioether compound and preparation method thereof
  • Aryl alkenyl thioether compound and preparation method thereof
  • Aryl alkenyl thioether compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Take 12mg (0.1mmol) of 4-fluorophenylacetylene, 14mg (0.2mmol) of ammonium thiocyanate, and 28mg (0.12mmol) of N-(4-methoxyphenylthio)succinimide into a 10mL reaction flask , then add 1 mL of hexafluoroisopropanol (HFIP), heat to 50°C, and stir for 12 hours. After the reaction, cool to room temperature, add 10 mL of ethyl acetate, add 5 mL of water for extraction, and dry the organic phase with anhydrous sodium sulfate. A light yellow liquid was obtained by column chromatography.

Embodiment 2

[0038] Take 12mg (0.1mmol) of 4-fluorophenylacetylene, 14mg (0.2mmol) of ammonium thiocyanate, and 28mg (0.12mmol) of N-(4-methoxyphenylthio)succinimide into a 10mL reaction flask , then add 1 mL of hexafluoroisopropanol (HFIP), heat to 80°C, and stir for 12 hours. After the reaction, cool to room temperature, add 10 mL of ethyl acetate, add 5 mL of water for extraction, and dry the organic phase with anhydrous sodium sulfate. A light yellow liquid was obtained by column chromatography.

Embodiment 3

[0040] Take 12mg (0.1mmol) of 4-fluorophenylacetylene, 14mg (0.2mmol) of ammonium thiocyanate, and 28mg (0.12mmol) of N-(4-methoxyphenylthio)succinimide into a 10mL reaction flask , then add 1 mL of hexafluoroisopropanol (HFIP), heat to 120°C, and stir for 12 hours. After the reaction, cool to room temperature, add 10 mL of ethyl acetate, add 5 mL of water for extraction, and dry the organic phase with anhydrous sodium sulfate. A light yellow liquid was obtained by column chromatography.

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Abstract

The invention discloses an aryl alkenyl thioether compound and a preparation method thereof. The aryl alkenyl thioether compound comprises a compound with a chemical formula as shown in the specification and acceptable salts, tautomers and stereoisomers thereof, and mixtures in all proportions. In the formula, R1 is one selected from a group consisting of hydrogen atoms, an alkyl group, a methoxylgroup, a halogen substituent, a cyano group, a nitro group, an aldehyde group and an ester group; R2 is an alkyl or phenyl group; and R3 represents a hydrogen atom, an alkyl group, a halogen atom orthe like. The invention provides a sulfur-containing compound. The preparation method has the advantages of simple operation, simple steps, a wide range of applicable substrates and simple post-treatment, and a solvent can be recycled.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to an aryl alkenyl sulfide compound and a preparation method thereof. Background technique [0002] In the process of compound synthesis and drug synthesis, the physicochemical and biological properties of drugs can be effectively adjusted by introducing sulfur atoms or sulfur-containing groups into compound molecules and drug molecules. Therefore, sulfur-containing compounds are extremely important in the fields of synthetic chemistry and medicinal chemistry. Organic synthesis intermediates, such as sulfur-containing cyano compounds as an important class of organic synthesis intermediates, can be further converted into trifluoromethylthio, mercaptans, thioethers, disulfides, sulfur-containing heterocycles and sulfur In addition, many antibacterial drugs and antiparasitic drugs contain thiocyano, and compounds containing thiocyano are of great significance in organic sy...

Claims

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Application Information

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IPC IPC(8): C07C331/04C07C331/10C07C331/14
CPCC07C331/04C07C331/10C07C331/14C07C2601/14
Inventor 刘世文
Owner YANCHENG INST OF TECH