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Method for preparing asymmetric disulfide

A disulfide, asymmetric technology, applied in the field of preparation of asymmetric disulfide N-phenyl-3-propionamide, can solve the problems of mercaptan odor, non-conforming to environmental protection, etc. mild effect

Active Publication Date: 2020-10-16
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there are mainly two methods for synthesizing asymmetric disulfides. The first method uses two different mercaptans as raw materials to synthesize asymmetric disulfides by oxidative dehydrogenation. The defect of this type of 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 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

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  • Method for preparing asymmetric disulfide
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  • Method for preparing asymmetric disulfide

Examples

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Effect test

specific Embodiment 1

[0014] Specific Example 1: Synthetic method: Add acetonitrile (10mL), 3-methylthio-N-phenylpropanamide (1mmol, 0.195g), diphenyl disulfide (1mmol, 0.218g) successively in a sealed tube of 50mL ) and N-fluorobisbenzenesulfonamide (1mmol, 0.315g), the reaction temperature was controlled at 80 degrees Celsius, and the reaction was vigorously stirred for 12 hours. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography in sequence to finally obtain N-phenyl-3-(phenyldisulfanyl)propanamide (0.187 g, 65%) as a pale yellow solid. The equations involved in the reaction are as follows:

[0015]

[0016] The NMR data and mass spectral data of the target product N-phenyl-3-(phenyldisulfanyl) propanamide are as follows:

[0017] 1 H NMR (300MHz, CDCl 3 )δ7.64–7.02(m,11H),3.06(t,J=6.8Hz,2H),2.71(t,J=6.9Hz,2H).

[0018] 13 C NMR (75MHz, CDCl 3 )δ169.08, 137.61, 137.16, 129.18, 129.02, 127.88, 127.18, 124.52, 120.07, 36.49, 34....

specific Embodiment 2

[0020] Specific example 2: comparative experiment: add acetonitrile (10mL), 3-methylthio-N-phenylpropanamide (1mmol, 0.195g) and diphenyl disulfide (1mmol, 0.218g) successively in a 50mL sealed tube ), the anti-temperature was controlled at 80 degrees centigrade, and the reaction was vigorously stirred for 12 hours. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography, but the target product N-phenyl-3-(phenyldisulfanyl)propionamide could not be separated. The equations involved in the reaction are as follows:

[0021]

specific Embodiment 3

[0022] Specific example 3: comparative experiment: add acetonitrile (10mL), 3-methylthio-N-phenylpropanamide (1mmol, 0.195g), diphenyl disulfide (1mmol, 0.218g) successively in a sealed tube of 50mL ) and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt [Selectfluor] (1mmol, 0.36g), and the reaction temperature was controlled at 80 degrees Celsius , and the reaction was vigorously stirred for 12 hours. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography, but the target product N-phenyl-3-(phenyldisulfanyl)propionamide could not be separated. The equations involved in the reaction are as follows:

[0023]

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Abstract

The invention relates to the technical field of fine chemical engineering, and discloses a method for preparing asymmetric disulfide. The preparation method comprises the following specific steps: taking 3-methylthio-N-phenylpropionamide and diphenyl disulfide as raw materials, taking N-fluorobisbenzenesulfonamide as an additive, and preferably carrying out a reaction in an acetonitrile solvent under a heating condition so as to obtain a target product, namely the symmetric disulfide N-phenyl-3-(phenyldithioalkyl)propionamide. The method is simple and convenient to operate and mild in reaction, 3-methylthio-N-phenylpropionamide and symmetric diphenyl disulfide are used as reaction raw materials, the asymmetric disulfide product is efficiently synthesized in one step, the use of a thiol rawmaterial with unpleasant smell or a transition metal catalyst is avoided, and the method has a potential application value.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and relates to a method for preparing unsymmetrical disulfide N-phenyl-3-(phenyldisulfanyl)propionamide. Background technique [0002] Unsymmetrical disulfides are an important class of organic compounds, and their parent skeletons are widely found in various natural products with pharmaceutical activity. At the same time, this compound is also an important intermediate in organic synthesis. Therefore, how to directly and efficiently synthesize such compounds has attracted great attention of chemists. [0003] At present, there are mainly two methods for synthesizing asymmetric disulfides. The first method uses two different mercaptans as raw materials to synthesize asymmetric disulfides by oxidative dehydrogenation. The defect of this type of 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;...

Claims

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Application Information

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IPC IPC(8): C07C323/62C07C319/24
CPCC07C323/62C07C319/24C07C323/60
Inventor 杨科宋梦杰李义李正义孙小强
Owner CHANGZHOU UNIV
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