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Sample method for synthesis of thianthrene based on sulfur powder

A technology of thianthrene and sulfur powder, which is applied in the field of environmentally friendly synthesis of thianthrene, achieving the effect of mild conditions and simple reaction operation

Inactive Publication Date: 2015-08-19
JIANGXI NORMAL UNIV
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Problems solved by technology

Because the synthesis of thioethers also needs to use thiophenol, these methods directly or indirectly require thiophenol as a raw material, and the pungent odor of this type of material and the environmental pollution caused in use have become the key points of the synthesis process. major restrictions

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  • Sample method for synthesis of thianthrene based on sulfur powder
  • Sample method for synthesis of thianthrene based on sulfur powder
  • Sample method for synthesis of thianthrene based on sulfur powder

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Embodiment Construction

[0009] The present invention is achieved in that in a 25 mL round bottom flask, add o-diiodobenzene (0.5 mmol), sulfur powder (0.5 mmol), cuprous iodide (0.05 mmol), 1,10-phenanthroline (0.1 mmol), potassium carbonate (1.0 mmol) and dimethyl sulfoxide (2 mL). The resulting mixed system is then 90 o C was stirred for 12 hours. After cooling to room temperature, 10 mL of water was added to the system, then extracted with ethyl acetate (3×10 mL), and dried over anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was subjected to silica gel column chromatography to obtain a pure product with a yield of 82%. The reaction formula and data are as follows figure 1 shown. The structure and purity of the obtained product were determined by proton nuclear magnetic resonance spectrum and carbon spectrum test and compared with literature data.

[0010] The proton nuclear magnetic resonance spectrum and carbon spectrum data of product thianthrene are:

[0...

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Abstract

A sample method for synthesis of thianthrene based on a sulfur powder comprises the steps: weighing 0.5 mmol of 1,2-diiodobenzene, 0.5 mmol of the sulfur powder, 0.05 mmol of cuprous iodide, 0.1 mmol of 1,10-phenanthroline and 1.0 mmol of potassium carbonate into a 25 mL round-bottom flask, adding a magnetic stirring bar and 2 mL of dimethyl sulfoxide, drying the obtained organic phase with anhydrous Na2SO4, filtering, evaporating to remove a solvent of the obtained filtrate, and separating and purifying the residue by silica gel column chromatography to obtain the thianthrene product. The method has the advantages: 1, raw materials are simple, and thiophenol or a derivative thereof having pungent smell has no need to be used; 2, the operation is simple, and any anhydrous and anaerobic operations and other special operations are not needed; and 3, reaction conditions are mild, the reaction can be completed by heating at 90 DEG C, and the thianthrene is suitable for magnified synthesis.

Description

technical field [0001] The invention relates to an environmentally friendly method for synthesizing thianthrene. Background technique [0002] As an intermediate in organic synthesis, thianthrene is characterized by a bis-benzoheterocyclic structure containing two sulfurs at the 1,4-position. These compounds play an important role in the field of organic chemistry. At the same time, studies have confirmed that thianthrene and its derivatives have diverse biological functions and drug activity habits, and are also key intermediates for the synthesis of various drugs. The currently known method for synthesizing thiophene is to use thiophenol derivatives or diphenyl sulfide derivatives as the main raw material, and obtain the target product through copper-catalyzed coupling reaction ring closure. Because the synthesis of thioethers also needs to use thiophenol, these methods directly or indirectly require thiophenol as a raw material, and the pungent odor of this type of mate...

Claims

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Application Information

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IPC IPC(8): C07D339/08
CPCC07D339/08
Inventor 万结平刘云云张毅
Owner JIANGXI NORMAL UNIV
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