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Aryl alkyl thioether compound and synthetic method thereof

A technology of aryl alkyl sulfide and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of sulfide, etc., and can solve problems such as expensive catalyst, easy oxidation of vulcanizing reagent, pungent smell of metal catalyst, etc. , to achieve the effect of no irritating odor, high reaction efficiency and mild conditions

Inactive Publication Date: 2014-09-17
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: vulcanizing reagents are easy to oxidize, easy to poison metal catalysts and have pungent odor, in addition, high temperature is required in the reaction process, the reaction solvent is an organic solvent, and the catalyst is relatively expensive

Method used

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  • Aryl alkyl thioether compound and synthetic method thereof
  • Aryl alkyl thioether compound and synthetic method thereof
  • Aryl alkyl thioether compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of benzyl (4-methoxyphenyl) sulfide:

[0040]

[0041] Catalyst CuI (3.8mg, 0.02mmol), ligand bipyridine L 1 (3.1mg, 0.02mmol), benzyl chloride (1mmol, 5equiv.) and Na 2 S 2 o 3 ·5H 2 O (248mg, 1mmol, 5equiv.) was added to the reaction tube, and then methanol / water (1mL / 1mL) was added as a reaction solvent, and stirred at a reaction temperature of 80°C for 2 hours. Then the temperature of the reaction system was lowered to 0°C in an ice bath, then triazene 1 (0.2 mmol, 1 equiv.) was added, and after stirring at room temperature for 15 minutes, BF was slowly added dropwise 3 ·Et 2 O (0.2 mmol, 1 equiv.). The reaction was then continued for 12 hours at room temperature. After the reaction was monitored by thin-layer chromatography, 5 mL of ethyl acetate was added to the reaction system and anhydrous sodium sulfate and anhydrous magnesium sulfate were added under continuous stirring. After stirring for five minutes, the mixture was filtered, and the fil...

Embodiment 2

[0043] Synthesis of benzyl (4-methoxyphenyl) sulfide:

[0044]

[0045] Catalyst CuCl (2.0mg, 0.02mmol), ligand bipyridine L 1 (3.1mg, 0.02mmol), benzyl chloride (1mmol, 5equiv.) and Na 2 S 2 o 3 ·5H 2 O (248mg, 1mmol, 5equiv.) was added to the reaction tube, and then methanol / water (1mL / 1mL) was added as a reaction solvent, and stirred at a reaction temperature of 80°C for 2 hours. Then the temperature of the reaction system was lowered to 0°C in an ice bath, then triazene 1 (0.2 mmol, 1 equiv.) was added, and after stirring at room temperature for 15 minutes, BF was slowly added dropwise 3 ·Et 2 O (0.2 mmol, 1 equiv.). The reaction was then continued for 12 hours at room temperature. After the reaction was monitored by thin-layer chromatography, 5 mL of ethyl acetate was added to the reaction system and anhydrous sodium sulfate and anhydrous magnesium sulfate were added under continuous stirring. After stirring for five minutes, the mixture was filtered, and the fi...

Embodiment 3

[0047] Synthesis of benzyl (4-methoxyphenyl) sulfide:

[0048]

[0049] Catalyst CuSO 4. 5H 2 O (2.0mg, 0.02mmol), ligand bipyridine L 1 (3.1mg, 0.02mmol), benzyl chloride (1mmol, 5equiv.) and Na 2 S 2 o 3 ·5H 2 O (248mg, 1mmol, 5equiv.) was added to the reaction tube, and then methanol / water (1mL / 1mL) was added as a reaction solvent, and stirred at a reaction temperature of 80°C for 2 hours. Then the temperature of the reaction system was lowered to 0°C in an ice bath, and triazene 1 (0.2 mmol, 1 equiv.) was added. After 15 minutes at room temperature, BF was slowly added dropwise. 3 ·Et 2 O (0.2 mmol, 1 equiv.). The reaction was then continued for 12 hours at room temperature. After the reaction was monitored by thin-layer chromatography, 5 mL of ethyl acetate was added to the reaction system and anhydrous sodium sulfate and anhydrous magnesium sulfate were added under continuous stirring. After stirring for five minutes, the mixture was filtered, and the filter ...

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Abstract

The invention discloses a synthetic method of an aryl alkyl thioether compound shown as formula (II), and the synthetic method is as follows: at room temperature and in a water phase, using triazene and haloalkane as reaction raw materials, using Na2S2O3 as a vulcanization reagent for reaction under the promotion effect of a copper catalyst and a Lewis acid to obtain the aryl alkyl thioether compound. The advantages of the synthetic method are as follows: reaction is efficient and yield is high; the vulcanization reagent is cheap, easy to obtain, stable, and free of irritating smell; the reaction is carried out in the solvent green water, the reaction is free of addition of a phase transfer catalyst and a volatile organic solvent, and is environmentally friendly; the reaction is carried out at room temperature, is mild in condition; the catalyst copper sulfate used in the reaction is cheap and economic reaction; the reaction substrate is easy in preparation; after amplification, the reaction efficiency is higher.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a class of aryl alkyl sulfide compounds and a green synthesis method thereof. Background technique [0002] Sulfur-containing organic compounds widely exist in biological structures and functional molecules. For example, there are sulfur-containing organic compounds in fruits and vegetables such as garlic, bananas, oranges, and strawberries. The essential amino acids cystine and cysteine ​​are also sulfur-containing compounds. . And it is widely used in the synthesis of medicine, polymer materials, pesticides, spices and flavors. There are more than 200 sulfur-containing drugs currently on the market, such as the anti-inflammatory drug Penicillins commonly used in daily life, Probucol for the treatment of cardiovascular diseases, the anti-HIV drug Nelfinavir, and the treatment of mental illness. The drug quetiapine fumarate (Quetiapine...

Claims

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Application Information

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IPC IPC(8): C07C323/09C07C323/20C07C323/48C07C323/62C07C323/07C07C321/28C07C323/56C07C319/14C07D213/70C07F5/04C07C317/22C07C315/02
Inventor 姜雪峰张永红李一鸣
Owner EAST CHINA NORMAL UNIV
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