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A kind of preparation method of 1,2-dithio-3-thione derivative synthesized by copper catalysis

A copper-catalyzed and derivative technology, applied in the field of preparation of 1,2-dithio-3-thione derivatives, can solve the problems of practicality and applicability limitations, harsh reaction conditions, difficult reaction conditions, etc. Effectiveness of operator health, reduced energy consumption, simplified process engineering

Inactive Publication Date: 2020-01-14
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the harsh conditions of these reactions, some of them need to be reacted at -78 ° C, the reaction conditions are difficult; some raw materials are not easy to prepare, and the economic cost is too high; various reasons have caused the practicability and applicability of these methods to be limited , cannot really be promoted on a large scale

Method used

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  • A kind of preparation method of 1,2-dithio-3-thione derivative synthesized by copper catalysis
  • A kind of preparation method of 1,2-dithio-3-thione derivative synthesized by copper catalysis

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Experimental program
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specific Embodiment 1

[0024] Specific embodiment one: with 41.3 milligrams (0.2mmol) (2-chloro-3,3,3-trifluoroprop-1-en-1-yl) benzene, 5.6 milligrams cuprous bromide (20mmol%), 76.9 milligrams (0.3mmol)S 8 , 9.3 mg (40% mmol) of tetramethylethylenediamine and 130.0 mg of cesium carbonate were added to 2 mL of solvent N,N-dimethylformamide. React at 120°C for 12 hours, cool down after the reaction, filter the reaction solution to obtain the filtrate; extract the filtrate twice with saturated sodium chloride solution, back-extract once, separate the obtained organic phase and dry it with anhydrous sodium sulfate. Filtrate again, and the filtrate is subjected to rotary evaporation, and the solvent is removed to obtain a residue. The residue is subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 30:1, and the effluent is collected according to the actual gradient. TLC Detect, combine the effluents containing the produc...

specific Embodiment 2

[0025] Specific embodiment two: 44.1 milligrams (0.2mmol) 1-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2-methylbenzene, 5.6 milligrams of cuprous bromide (20mmol%), 76.9 mg (0.3mmol) S 8 , 9.3 mg (40% mmol) of tetramethylethylenediamine and 130.0 mg of cesium carbonate were added to 2 mL of solvent N,N-dimethylformamide. React at 120°C for 12 hours, cool down after the reaction, filter the reaction solution to obtain the filtrate; extract the filtrate twice with saturated sodium chloride solution, back-extract once, separate the obtained organic phase and dry it with anhydrous sodium sulfate. Filtrate again, and the filtrate is subjected to rotary evaporation, and the solvent is removed to obtain a residue. The residue is subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 30:1, and the effluent is collected according to the actual gradient. TLC Detect, combine the effluents containing the produ...

specific Embodiment 3

[0026] Specific embodiment three: 44.1 milligrams (0.2mmol) 1-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-3-methylbenzene, 5.6 milligrams of cuprous bromide (20mmol%), 76.9 mg (0.3mmol) S 8 , 9.3 mg (40% mmol) of tetramethylethylenediamine and 130.0 mg of cesium carbonate were added to 2 mL of solvent N,N-dimethylformamide. React at 120°C for 12 hours, cool down after the reaction, filter the reaction solution to obtain the filtrate; extract the filtrate twice with saturated sodium chloride solution, back-extract once, separate the obtained organic phase and dry it with anhydrous sodium sulfate. Filtrate again, and the filtrate is subjected to rotary evaporation, and the solvent is removed to obtain a residue. The residue is subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 30:1, and the effluent is collected according to the actual gradient. TLC Detect, combine the effluents containing the pro...

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Abstract

The invention discloses a 1,2-dithio-3-thioketone derivative synthesized by cyclizing of fluorine-sulfur removal of trifluoropropyne via copper catalyzing. The 1,2-dithio-3-thioketone derivative is prepared by the following steps of using a 2-chloro-3,3,3-trifluoro-1 propene compound as a primer; adding cuprous bromide as a catalyst into the primer, using cesium carbonate as alkaline, using tetramethylethylenediamine as a ligand, using elemental sulfur as a sulfur source, and stirring to react for 12 hours in a N,N-dimethyl formamide solvent at the temperature of 120 DEG C; after reaction is finished, filtering a reaction liquid, extracting a filtrate twice by a saturated sodium chloride solution, reversely extracting once, separating to obtain an organic phase, and drying with anhydrous sodium sulfate; filtering again, and removing the solvent out of the filtrate by a rotary evaporator, so as to obtain the remaining matter; performing column chromatography separating on the remainingmatter by a silicon gel column, spraying by an elution solution, and collecting an effluent solution containing the target product; combining the effluent solution, concentrating under the vacuum condition, and removing the solvent, so as to obtain the target product. The 1,2-dithio-3-thioketone derivative has the advantages that the raw materials are simple and are easy to obtain, the preparationtechnology is novel and simple, the pollution is little, the energy consumption is low, and the yield rate is high.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for preparing 1,2-dithio-3-thione derivatives synthesized by copper catalysis. Background technique [0002] 1,2-Dithio-3-thione is an important building block of various drugs with remarkable biological and medicinal properties, including chemotherapeutic, antioxidant and radioprotective effects. For example, Otipraz has anti-HIV activity (see Biochem.Biophys.Res.Comm.1996,221,548), NOSH-1 shows excellent anti-inflammatory effect (ACSMed.Chem.Lett.2012,3,257), S- Danshensu has a certain therapeutic effect on male infertility (CN 102417501A), and anetetithione ADT is used as a choleretic (Rev. Suisse Praxis Med. 1979, 68, 1063). [0003] In the prior art, 1,2-dithio-3-thione was synthesized by terminal alkynes with CS 2 and S 8 Obtained in a multistep reaction at -78°C (Tetrahedron Lett. 2014, 55, 5283). or through β-ketoesters or ketones with specific vulcanization ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D339/04C07D409/04
CPCC07D339/04C07D409/04
Inventor 张兴国韦锋张小红胡伯伦邓辰亮
Owner WENZHOU UNIV