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Method for synthesizing organic sulfur compound under condition without solvent

A compound and carbonyl compound technology, applied in the field of environment-friendly synthesis, can solve the problems of harming the health of users, volatile penetration, inconvenient transportation, etc., and achieve the effect of mild reaction conditions, low price, and easy process

Inactive Publication Date: 2005-10-26
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Low-molecular-weight mercaptans are often used in the reaction. This kind of thiol reagent is not only expensive, toxic, and inconvenient to transport, but also volatile, has an unbearable odor, and has a strong penetrating odor. It is easy to cause environmental pollution and damage users. health
With the increasing attention to environmental issues around the world, some researchers have begun to devote themselves to the non-toxic and odorless transformation of thiol reagents, such as increasing the length of the alkyl chain, introducing silyl groups on the aromatic ring, and thiols with high Molecularization, etc. (①Tetradedron Lett.2001, 42, 9207; ②J.Org.Chem.2000, 65, 4839.), but this kind of odorless thiol itself is mostly prepared by small molecule thiol or other toxic sulfur-containing reagents, That is, failure to solve the problem from the source

Method used

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  • Method for synthesizing organic sulfur compound under condition without solvent
  • Method for synthesizing organic sulfur compound under condition without solvent
  • Method for synthesizing organic sulfur compound under condition without solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In a 50 ml round bottom flask, add 0.404 g (2 mmol) 3-(1,2-ethylenedithio)methylene-2,4-pentanedione, 0.302 g (2 mmol) 4- Nitrobenzaldehyde, 0.702 (2.15 mmol) grams of dodecylbenzenesulfonic acid, heated to 50 ° C, stirred for 45 minutes, TLC monitoring to the disappearance of 4-nitrobenzaldehyde, through column chromatography, a white solid 2- (4-nitrophenyl)-[1,3]dithiapentane 0.396 g, yield 87.2%. The reaction is shown in the following formula:

[0028]

Embodiment 2

[0030] In a 50 ml round bottom flask, add 0.404 g (2 mmol) 3-(1,2-ethylenedithio)methylene-2,4-pentanedione, 0.302 g (2 mmol) 4- Nitrobenzaldehyde, 0.702 g (2.15 mmol) dodecylbenzenesulfonic acid, stirred at 20°C for 150 minutes, monitored by TLC until 4-nitrobenzaldehyde disappeared, after column chromatography, a white solid was obtained to obtain 2- (4-nitrophenyl)-[1,3]dithiapentane 0.368 g, yield 81.1%. The reaction is shown in the following formula:

[0031]

Embodiment 3

[0033] In a 50 ml round bottom flask, add 0.404 g (2 mmol) 3-(1,2-ethylenedithio)methylene-2,4-pentanedione, 0.302 g (2 mmol) 4- Nitrobenzaldehyde, 0.702 g (2.15 mmol) dodecylbenzenesulfonic acid, heated to 100 ° C, stirred for 15 minutes, TLC monitoring to the disappearance of 4-nitrobenzaldehyde, through column chromatography, a white solid was obtained to obtain 2 -(4-nitrophenyl)-[1,3]dithiapentane 0.408 g, yield 89.9%. The reaction is shown in the following formula:

[0034]

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PUM

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Abstract

The present invention provides an environment-protecting type synthesis method for synthesizing organic sulfur compound under the solvent-free condition by using inodorous thioketenes compound as sulfur source reagent and adding organic acid or inorganic acid as catalyst so as to implement synthesis of series organic sulfur compounds.

Description

Technical field: [0001] The invention belongs to an organic synthesis method, and in particular relates to an environment-friendly synthesis method using a thioketene compound as a sulfur source reagent and synthesizing an organic sulfur compound under a solvent-free condition. Background technique: [0002] Organosulfur compounds, such as thioacetals / ketones, thioethers, thienes, etc., are commonly used chemical reagents in laboratories and synthetic precursors or intermediates in organic synthetic chemistry. At the same time, organosulfur compounds are important chemical raw materials, and have a very wide range of applications in the fields of medicine, pesticides, and spices. There are many ways to synthesize organosulfur compounds, such as the condensation reaction of mercaptans and aldehydes / ketones catalyzed by different acids (protonic acid, Lewis acid, solid acid, etc.), the addition reaction with unsaturated olefins, and the reaction with halogenated Alkylation re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/06
Inventor 欧阳艳董德文刘群于海丰王芒张前
Owner NORTHEAST NORMAL UNIVERSITY
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