Preparation method of substituted thiophenol

A technology of thiophenol and halogenated benzene, which is applied in the field of preparation of substituted thiophenols, can solve the problems of high reaction conditions, high production costs, and high requirements for reaction conditions, and achieve simple preparation process, low environmental pollution, and high product yield high effect

Inactive Publication Date: 2005-03-09
ZHEJIANG UNIV OF TECH
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Problems solved by technology

The reaction conditions of the diazotization method are relatively high, the process route is long, and the yield is not high; the cost of the dealkylation method using sulfide is high, and further research is needed for industrial production; the sulfuryl chloride reduction method uses iron powder or zinc powder During the reduction process, a large amount of waste residue and sewage are generated
The preparation of substituted thiophenols by substitution reaction is a promising synthetic route, but the reaction conditions for the preparation of thiophenols by the substitution method currently reported are generally high and have certain limitations. For example, U.S. Patent US4284817 provides a method using benzene A method for preparing thiophenols by substituting hydrogen sulfide with hydrogen sulfide, but this method requires a temperature as high as 500 ° C to 900 ° C, and requires a high-absorption catalyst such as activated carbon, etc., and the production cost is high

Method used

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  • Preparation method of substituted thiophenol
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  • Preparation method of substituted thiophenol

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1 Preparation of p-trifluoromethylthiophenol

[0021] 18 grams (0.1 moles) of p-trifluoromethylchlorobenzene and 28 grams (0.5 moles) of industrial sodium hydrosulfide pulverized are placed in a 500 milliliter three-necked flask, and 150 grams of solvent N, N-dimethylacetamide are added , heated and stirred, and reacted at 120° C. for 15 hours. After the reaction was completed, it was cooled, and dilute sulfuric acid was gradually added under stirring to acidify to pH=3. After steam distillation, 14.6 g of slightly light yellow transparent liquid was distilled out, with a yield of 82%. Boiling range 64~66°C (13 mm Hg), purity ≥98%, MS (m / z): 178 (M + ).

Embodiment 2

[0022] Embodiment 2 Preparation of p-nitrothiophenol

[0023] 15.8 grams (0.1 mole) of p-nitrochlorobenzene and 56 grams (1.0 mole) of industrial product sodium hydrosulfide of pulverization are placed in a 500 milliliter three-necked flask, and 150 grams of solvent N, N-dimethylformamide are added, heated Stir and react at 100°C for 10 hours. After the reaction was completed, it was cooled, and dilute sulfuric acid was gradually added under stirring to acidify to pH=3. Steam distillation yielded 13.9 g of light yellow solid with a yield of 90%. Melting point 77~81℃, purity ≥98%, MS(m / z): 155(M + ).

Embodiment 3

[0024] Embodiment 3 3, the preparation of 5-bis (trifluoromethyl) thiophenol

[0025] Put 24.9 grams (0.1 mole) of 3,5-bis(trifluoromethyl)chlorobenzene and 28 grams (0.5 mole) of industrial sodium hydrosulfide into a 500-milliliter three-necked flask, and add the solvent dimethyl sulfoxide 180 grams, heated and stirred, and reacted at 110°C for 10 hours. After the reaction was completed, it was cooled, and dilute sulfuric acid was gradually added under stirring to acidify to pH=4. After steam distillation, 19.7 g of slightly light yellow transparent liquid was distilled out, with a yield of 80%. Boiling point 63~65℃(15mm Hg), purity ≥98%, MS(m / z): 246(M + ).

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Abstract

A process for preparing substituted benzenethiol includes such steps as reaction between substituted halobenzene and thiohydrogenating reagent in non-protonic polar solvent while stirring, acidifying to pH=1-6, and distilling.

Description

(1) Technical field [0001] The invention relates to a preparation method of substituted thiophenols, in particular to a method for preparing electron-withdrawing substituted thiophenols by substitution reaction. (2) Technical background [0002] Substituted thiophenols are an important class of organic compounds, widely used in medicine, pesticides, dyes and other industries, and can be used to synthesize thrombin inhibitors, fungicides, dermatitis drugs, herbicides, corrosion inhibitors and photosensitive materials. In the current technology, the preparation of substituted thiophenols mainly includes the diazotization method, the dealkylation method of thioether, and the reduction method of sulfonyl chloride. The reaction conditions of the diazotization method are relatively high, the process route is long, and the yield is not high; the cost of the dealkylation method using sulfide is high, and further research is needed for industrial production; the sulfuryl chloride red...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/02C07C321/26
Inventor 裴文孙莉
Owner ZHEJIANG UNIV OF TECH
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