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Application of ketene thioacetal derivatives as thioalcohol substituted reagent

A technology of thioketal and derivatives, applied in the application field of environment-friendly organic reagents in organic synthesis

Inactive Publication Date: 2005-03-16
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of these odorless thiol reagents itself has adopted small molecule thiols or other toxic sulfur-containing reagents, failing to solve the original problem from the source

Method used

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  • Application of ketene thioacetal derivatives as thioalcohol substituted reagent
  • Application of ketene thioacetal derivatives as thioalcohol substituted reagent
  • Application of ketene thioacetal derivatives as thioalcohol substituted reagent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a 50 ml round bottom flask, add 0.648 g (2 mmol) of 2-(1,3 propylenedithio) methylene-butyric acid methyl ester-3-ketone and 2 mmol of benzaldehyde, then, add 10 milliliters of ethanol was stirred, and then 0.712 milliliters of acetyl chloride was added, heated to reflux, monitored by TLC until the benzaldehyde disappeared, the ethanol was distilled off under reduced pressure, and column chromatography gave 2-phenyl-[1,3]dithiane as a white solid. Yield: 84.1%. The reaction is shown in the following formula:

[0041]

Embodiment 2

[0043] In a 50 ml round bottom flask, add 0.404 g (2 mmol) of 3-(1,2-ethylenedithio)methylene-2,4-pentanedione and 0.302 g (2 mmol) of 4- Nitrobenzaldehyde, then, add 10 milliliters of methanol, stir, then add 0.712 milliliters of acetyl chloride, heat to reflux, TLC monitors until 4-nitrobenzaldehyde disappears, evaporate methanol under reduced pressure, and column chromatography gives a white solid to obtain 2 -(4-nitrophenyl)-[1,3]dithiapentane 0.380 g, yield 83.5%. The reaction is shown in the following formula:

[0044]

Embodiment 3

[0046] In a 50 ml round bottom flask, add 0.432 g (2 mmol) of 3-(1,3-propylenedithio)methylene-2,4-pentanedione, 0.212 g (2 mmol) of benzaldehyde and 0.240 grams (2 mmol) of acetophenone, then add 10 milliliters of methanol, stir, then add 0.5 milliliters of acetyl chloride, heat to reflux, TLC monitors the reaction for 3 hours, evaporates methanol under reduced pressure, and column chromatography gives white solid 2 -0.383 g of phenyl-[1,3]dithiane, the yield was 91.3%, and 0.218 g (95%) of acetophenone was recovered at the same time. The reaction is shown in the following formula:

[0047]

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Abstract

The invention relates to the use of ketene thioacetal derivatives in organic synthesis as thioalcohol substituted environment-friendly type organic reagent, wherein thioalcohol has strong volatility, irritation bad odor, toxicity and carcinogenic action, aiming at solving this problem, the invention employs ketene thioacetal derivatives as thioalcohol substituted reagent to realize the synthesizing of sulfur-containing compounds.

Description

Technical field: [0001] The invention belongs to the application of organic reagents, in particular to the application of a thioketene derivative as an environment-friendly organic reagent used instead of thiol in organic synthesis. Background technique: [0002] Thiols are commonly used organic reagents and can be used as synthetic precursors or intermediates in various organic synthesis reactions, such as: carbonyl protection reagents for carbonyl compounds such as aldehydes and ketones and their derivatives, nucleophilic Reagents, particle dispersants in the synthesis of nanomaterials, etc., are also the basic raw materials for the synthesis of many chemicals such as drugs, pesticides, and spices. [0003] However, mercaptans (especially low-molecular-weight mercaptans) have strong volatility, pungent odor and greater toxicity. From the source, the sulfur sources for preparing mercaptans, such as hydrogen sulfide, sodium hydrosulfide, sulfur Urea and thioacetate are also...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/00C07C323/22C07D339/00C07D339/06C07D339/08
Inventor 刘群董德文于海丰欧阳艳刘军王芒方群欣李春仁
Owner NORTHEAST NORMAL UNIVERSITY
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