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Preparation method of diphenyl disulfide compounds

A technology of diphenyl disulfide and compounds, which is applied in the field of preparation of high-purity organic intermediates, can solve the problems of large environmental pollution, high requirements for reaction conditions, and long synthetic routes, and achieve pollution reduction, improved reactivity, and synthetic routes. short effect

Active Publication Date: 2020-10-13
WUHAN INSTITUTE OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process of using thiophenol as the starting material has a long synthesis route, high requirements on reaction conditions, and great environmental pollution

Method used

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  • Preparation method of diphenyl disulfide compounds
  • Preparation method of diphenyl disulfide compounds
  • Preparation method of diphenyl disulfide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1. Synthesis of diphenyl disulfide

[0039]

[0040] Add 100 mL of tetrahydrofuran to a pre-dried reaction flask filled with nitrogen (or argon), cool the mixture to -78°C, then add iodobenzene (0.1 mol), and slowly add isopropyl Magnesium chloride (0.11mol), the reaction solution was stirred at -78°C to -20°C, and the reaction progress was monitored by gas chromatography. After about 30-90 minutes, the halogen-magnesium exchange reaction was completed. Then dichlorodisulfur (0.05mol) was added to the reaction system, and the reaction solution was slowly raised to room temperature, and the reaction was quenched with saturated ammonium chloride solution, and the organic phase was extracted with ether or ethyl acetate, and dried with anhydrous magnesium sulfate The organic phase was concentrated and the organic phase was concentrated to obtain 9.7 g of white solid diphenyl disulfide with a yield of 89% and a purity of ≥95%. figure 1 Be the synthetic diphenyl ...

Embodiment 2

[0044] Example 2. Synthesis of p-methyldiphenyl disulfide

[0045]

[0046] Add 100 mL of tetrahydrofuran to a pre-dried reaction flask filled with nitrogen (or argon), cool the mixture to -78°C, then add p-methyliodobenzene (0.1 mol), and slowly add Isopropylmagnesium chloride (0.11mol), the reaction solution was stirred at -78°C to -20°C, and the reaction progress was monitored by gas chromatography. The halogen-magnesium exchange reaction was completed after about 30-90 minutes. Then dichlorodisulfur (0.05mol) was added to the reaction system, and the reaction solution was slowly raised to room temperature, and the reaction was quenched with saturated ammonium chloride solution, and the organic phase was extracted with ether or ethyl acetate, and dried with anhydrous magnesium sulfate Concentrate the organic phase to obtain 10.8 g of p-methyl diphenyl disulfide as a yellow solid, with a yield of 88% and a purity of ≥95%. image 3 It is the p-methyl diphenyl disulfide s...

Embodiment 3

[0051]Example 3. Synthesis of p-Methoxydiphenyl Disulfide

[0052]

[0053] Add 100 mL of tetrahydrofuran to a pre-dried reaction flask filled with nitrogen (or argon), cool the mixture to -78°C, then add p-methoxyiodobenzene (0.1 mol), and slowly add to the reaction liquid droplet Add isopropylmagnesium chloride (0.11mol), and stir the reaction solution at -78°C to -20°C, and monitor the progress of the reaction by gas chromatography. After about 30-90 minutes, the halogen-magnesium exchange reaction ends. Then dichlorodisulfide (0.05mol) was added to the reaction system, and the reaction solution was slowly raised to room temperature, and the reaction was quenched with saturated ammonium chloride solution, and the organic phase was extracted with ether or ethyl acetate, and dried with anhydrous magnesium sulfate Concentrate the organic phase to obtain 12.7 g of light yellow solid p-methoxydiphenyl disulfide with a yield of 91% and a purity of ≥95%. Figure 5 It is the p...

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Abstract

The invention discloses a preparation method of diphenyl disulfide compounds. The preparation method comprises the following steps: stirring an isopropyl magnesium halide Grignard reagent and a substituted halogen benzene compound in an organic solvent at -78 DEG C to -20 DEG C for 30-90 minutes to obtain a thoroughly halogen-magnesium exchanged substituted phenyl Grignard reagent; and adding dichlorodisulfide into the reaction system, slowly heating to room temperature after the reaction is finished, quenching the reaction by using a saturated ammonium chloride aqueous solution, extracting byusing ethyl acetate or diethyl ether, drying by using anhydrous magnesium sulfate, and concentrating the organic phase to obtain the diphenyl disulfide compounds. According to the method, the diphenyl disulfide compounds are prepared by taking the phenyl Grignard reagent as a raw material through a one-pot method, and has the following advantages: the synthetic route is short, the preparation process is simple, the cost is low, the operation is easy, the yield is excellent, and the industrial production is easy.

Description

technical field [0001] The invention relates to the preparation of high-purity organic intermediates, in particular to a method for preparing substituted diphenyl disulfide compounds in two steps and one pot using substituted halobenzene, isopropylmagnesium halide and disulfide dichloride as raw materials . Background technique [0002] Diphenyl disulfide is an important class of pharmaceutical intermediates, widely used in medicine, pesticides, dye intermediates, chemicals and other fields. The current preparation and synthesis methods of diphenyl disulfide all use thiophenol as a raw material, which is a colorless liquid with a foul smell at normal temperature, active in chemical properties, highly toxic and explosive. The process of using thiophenol as the starting material has a long synthesis route, high requirements on reaction conditions, and great environmental pollution. Contents of the invention [0003] Based on the above deficiencies in the prior art, the tec...

Claims

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Application Information

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IPC IPC(8): C07C321/28C07C323/20C07C319/22C07C319/28
CPCC07C321/28C07C323/20C07C319/22C07C319/28C07F3/02
Inventor 董志兵王曦
Owner WUHAN INSTITUTE OF TECHNOLOGY
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