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Method for synthesizing asymmetric cyanoalkyl disulfide

A technology of cyanoalkyl disulfide and cyanoalkyl disulfide, which is applied in the field of synthesis of asymmetric cyanoalkyl disulfide, which can solve the problem of environmentally unfriendly irritating odor, difficulty in large-scale production, and environmental pollution and other issues, to achieve the effect of low price, easy access, and simple post-processing

Active Publication Date: 2019-11-12
中国人民解放军军事科学院防化研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (2) Most reactions use mercaptan as a sulfur source, and mercaptan is an environmentally unfriendly reagent with a relatively pungent odor, which will cause certain potential toxicity to the human body and is not easy to scale production
[0007] (3) Organic solvents are more or less toxic and expensive, causing certain pollution to the environment
Jiang Xuefeng's research group has also carried out corresponding research on unsymmetrical aryl alkyl disulfides, using sodium thiosulfate as the sulfur source, and obtaining the target product through redox methods, but this method is only applicable to the synthesis of aryl sulfides. Synthetic, and the solvent used is dioxane, which has certain toxicity

Method used

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  • Method for synthesizing asymmetric cyanoalkyl disulfide
  • Method for synthesizing asymmetric cyanoalkyl disulfide
  • Method for synthesizing asymmetric cyanoalkyl disulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Preparation of 4-(hexyldithio)butyronitrile

[0057]

[0058] In a 10mL reaction bottle equipped with a magnet, add 4-cyanobutyl sodium thiosulfate (203mg, 1mmol, 1.25equiv.), thiourea (73mg, 0.96mmol, 1.20equiv.), sodium carbonate (102mg , 0.96mmol, 1.20equiv.), sodium dodecylbenzenesulfonate (34.8mg, 0.1mmol, 0.125equiv.), 1-bromohexane (132mg, 0.8mmol, 1equiv.) and water (1mL), in Under the protection of nitrogen, the reaction was stirred at 80° C. for 7 hours. The reaction was cooled to room temperature, 5 mL of water was added, the mixture was extracted with ethyl acetate (15 mL×3), the organic phases were combined, dried with 4 g of anhydrous magnesium sulfate, filtered through filter paper, and vacuum reduced (vacuum degree 95 mmHg, heating temperature 48 ° C) The solvent was removed, and 4-(hexyldithio)butyronitrile was obtained after separation by column chromatography (eluent polarity: petroleum ether / ethyl acetate 20:1). Yield: 83%; 1 H NMR (300MHz, CD ...

Embodiment 2

[0060] Preparation of 4-(hexyldithio)butyronitrile

[0061]

[0062] In a 10mL reaction bottle equipped with a magnet, add 4-cyanobutyl sodium thiosulfate (203mg, 1mmol, 1.25equiv.), thiourea (73mg, 0.96mmol, 1.20equiv.), sodium carbonate (102mg , 0.96mmol, 1.20equiv.), sodium dodecylbenzenesulfonate (34.8mg, 0.1mmol, 0.125equiv.), 1-iodohexane (169mg, 0.8mmol, 1equiv.) and water (1mL), in Under the protection of nitrogen, the reaction was stirred at 80° C. for 7 hours. The reaction was cooled to room temperature, 5 mL of water was added, the mixture was extracted with ethyl acetate (15 mL×3), the organic phases were combined, dried with 4 g of anhydrous magnesium sulfate, filtered through filter paper, and vacuum reduced (vacuum degree 95 mmHg, heating temperature 48 ° C) The solvent was removed, and 4-(hexyldithio)butyronitrile was obtained after separation by column chromatography (eluent polarity: petroleum ether / ethyl acetate 20:1). Yield: 89%; 1 H NMR, 13 C NMR an...

Embodiment 3

[0065] Preparation of 4-(heptyldithio)butyronitrile

[0066]

[0067] In a 10mL reaction bottle equipped with a magnet, add 4-cyanobutyl sodium thiosulfate (203mg, 1mmol, 1.25equiv.), thiourea (73mg, 0.96mmol, 1.20equiv.), sodium carbonate (102mg , 0.96mmol, 1.20equiv.), sodium dodecylbenzenesulfonate (34.8mg, 0.1mmol, 0.125equiv.), 1-bromoheptane (142mg, 0.8mmol, 1equiv.) and water (1mL), in Under the protection of nitrogen, the reaction was stirred at 80° C. for 7 hours. The reaction was cooled to room temperature, 5 mL of water was added, the mixture was extracted with ethyl acetate (15 mL×3), the organic phases were combined, dried with 4 g of anhydrous magnesium sulfate, filtered through filter paper, and vacuum reduced (vacuum degree 95 mmHg, heating temperature 48 ° C) The solvent was removed, and 4-(heptyldithio)butyronitrile was obtained after separation by column chromatography (eluent polarity: petroleum ether / ethyl acetate 20:1). Yield: 76%; 1 H NMR (300MHz, ...

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Abstract

The invention relates to a method for synthesizing asymmetric cyanoalkyl disulfide, which comprises the following step of: conducting reacting on thiourea and alkyl Bunte salt serving as sulfur sources, an alkyl halide serving as a raw material, sodium dodecyl benzene sulfonate serving as an auxiliary reagent and sodium carbonate serving as alkali in water to obtain an asymmetric cyanoalkyl disulfide compound. According to the method, mercaptan with pungent smell is prevented from being used as a sulfur source, the purpose of friendliness and environmental protection is achieved, meanwhile, the reaction operation is simple, the reaction conditions are mild, and the method is suitable for large-scale production.

Description

technical field [0001] The invention relates to a method for synthesizing unsymmetrical cyanoalkyl disulfides. Background technique [0002] Sulfur chemistry has gained considerable attention over the past few decades. Sulfur-containing compounds are widely used in various fields such as pharmacy, agriculture and chemistry. In addition, organosulfur compounds also have a significant impact in the field of materials, for example, sulfur atoms have strong forces on both the physical and electronic surfaces of some materials. Sulfur-containing compounds exist in natural products, especially marine natural products. The metabolites of marine organisms have great scientific research value, and effective medicinal molecules can be screened out through their research. For example, a class of natural product thiodiketopiperazine (Epidithiodiketopiperazine, ETP) with a unique structure shows superior activity against poliovirus. Therefore, the method of constructing asymmetric di...

Claims

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Application Information

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IPC IPC(8): C07C319/22C07C323/52
CPCC07C319/22C07C2601/08C07C2601/14C07C323/52
Inventor 王红梅卢晓刚符飞燕高润利
Owner 中国人民解放军军事科学院防化研究院
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