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Method for catalytically synthesizing asymmetric disulfide derivative by NFSI

A technology of disulfides and derivatives, which is applied in the field of NFSI catalytic synthesis of asymmetric disulfide derivatives, can solve the problems of use, limited application, and incompatible with green environmental protection.

Active Publication Date: 2021-10-29
CHANGZHOU UNIV
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are two main methods for the preparation of asymmetric disulfides. The first method uses two different mercaptans as raw materials to synthesize asymmetric disulfides by oxidative dehydrogenation. The disadvantage of this method is that the mercaptans have an unpleasant smell. , at the same time, this type of reaction will undergo self-coupling to obtain a symmetrical disulfide; the second type uses a disulfide reagent to react with a nucleophile under the action of a transition metal catalyst to obtain the target product. The defect of this type of reaction mainly lies in the use of metal Catalyst, does not meet the characteristics of green environmental protection
In addition, the use of transition metal rhodium catalysts can also realize the exchange reaction between symmetrical disulfide compounds to synthesize asymmetric disulfide derivatives, but the application of this strategy is limited due to the use of expensive rhodium catalysts.

Method used

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  • Method for catalytically synthesizing asymmetric disulfide derivative by NFSI
  • Method for catalytically synthesizing asymmetric disulfide derivative by NFSI
  • Method for catalytically synthesizing asymmetric disulfide derivative by NFSI

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Experimental program
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Embodiment 1

[0019] The reaction equation that embodiment 1 relates to is as follows:

[0020]

[0021] Synthesis of unsymmetrical disulfide derivatives: Add 1,2-dichloroethane (10 mL), symmetrical disulfide A (1.0 mmol), symmetrical disulfide B ( 1.0mmol) and NFSI (0.1mmol), the reaction temperature was controlled at 50 degrees Celsius, and the reaction was vigorously stirred for 4 hours. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography in sequence to obtain the unsymmetrical disulfide derivative.

[0022] 1. According to the above experimental conditions, a series of unsymmetrical disulfides were synthesized, the structures and yields are as follows:

[0023]

[0024] 2. NMR and mass spectrometry data:

[0025] (1) Compound C1: 1 H NMR (300MHz, Chloroform-d) δ7.53–7.48(m,2H),6.92–6.87(m,2H),3.80(s,3H),2.45(s,3H). 13 C NMR (75MHz, Chloroform-d) δ159.76, 132.16, 127.81, 114.77, 55.44, 22.94. MS (EI): m / z = 185.9 [M + ]...

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Abstract

The invention belongs to the field of fine chemical engineering, and relates to a method for catalytically synthesizing an asymmetric disulfide derivative by NFSI. The method comprises the steps of adding NFSI, symmetric disulfide A and symmetric disulfide B into a sealed tube containing a reaction solvent 1, 2-dichloroethane, reacting at the temperature of 25-80 DEG C for 1-8 hours, ending the reaction, and separating and purifying to obtain the asymmetric disulfide derivative, wherein the molar ratio of the NFSI to the symmetric disulfide A to the symmetric disulfide B is 0.1: 1.0: 1.0. According to the method, the asymmetric disulfide derivative can be efficiently synthesized without using an expensive rhodium metal catalyst and odorous mercaptan.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and relates to a method for catalyzing and synthesizing asymmetric disulfide derivatives by NFSI. Background technique [0002] Asymmetric disulfides are an important class of sulfur-containing organic compounds, which widely exist in various natural products, drugs, foods and materials with pharmaceutical activity. Therefore, how to directly and efficiently synthesize such compounds has attracted great attention of chemists. There are two main methods for the preparation of asymmetric disulfides. The first method uses two different mercaptans as raw materials to synthesize asymmetric disulfides through oxidative dehydrogenation. The disadvantage of this method is that the smell of mercaptans is unpleasant. , At the same time, this type of reaction will undergo self-coupling to obtain a symmetrical disulfide; the second type uses a disulfide reagent to react with a nucleophile under the act...

Claims

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Application Information

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IPC IPC(8): C07C323/20C07C323/09C07C321/20C07C319/24C07D277/78
CPCC07C319/24C07D277/78C07C323/20C07C323/09C07C321/20
Inventor 杨科胡倾月宋梦杰张菲杨李正义孙小强
Owner CHANGZHOU UNIV
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