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Synthesis method of 3-substituent diphenyl sulfide

A technology of diphenyl sulfide and synthesis method, which is applied in the preparation of sulfide, hydrogenated polysulfide/polysulfide, organic chemistry, etc., can solve the problems of unstable thiophenol, difficult synthesis, low yield and the like

Pending Publication Date: 2021-09-14
江西扬帆新材料有限公司
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Problems solved by technology

[0008] 3-Methoxy diphenyl sulfide can be obtained by methods A and B; while 3-hydroxy diphenyl sulfide is difficult to synthesize. On the one hand, thiophenol containing phenolic hydroxyl is very unstable and easily oxidized; On the one hand, if method B is adopted, compounds containing phenolic hydroxyl groups are also easy to form azo compounds with diazonium salts, resulting in low yield and difficult purification, so it is difficult to carry out truly effective industrial production of 3-hydroxydiphenyl sulfide

Method used

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  • Synthesis method of 3-substituent diphenyl sulfide
  • Synthesis method of 3-substituent diphenyl sulfide
  • Synthesis method of 3-substituent diphenyl sulfide

Examples

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Embodiment 1

[0048] The synthesis of embodiment 1,3-hydroxyl diphenyl monosulfide

[0049] 150 grams of 70% H 2 SO 4 Aqueous solution (H 2 SO 4 1.07 mol), 20.1 g of 3-aminodiphenyl monosulfide (0.1 mol), the temperature was raised to 210° C., and the reaction was maintained for 6 hours.

[0050] After the reaction was finished, it was cooled to room temperature, and 200 grams of water was added to dilute sulfuric acid, and a brown solid was precipitated. After suction filtration, the filter cake (brown solid) was washed once with 200ml of water. The washed filter cake was dropped into 180 grams of 5% liquid caustic soda (i.e. a NaOH solution with a mass concentration of 5%) and was heated to 80° C. for dissolution, and 0.5 gram of activated carbon was added to insulate for 30 minutes. After suction filtration, about 20 g of 36% hydrochloric acid (the pH value is about 3-4 at this time) was added dropwise to the filtrate, and a light brown powder was precipitated. After suction filtra...

Embodiment 2、3

[0056] Embodiment 2,3, the synthesis of 3'-dihydroxy diphenyl disulfide

[0057] 200 grams of 65% H 2 SO 4 Aqueous solution (H 2 SO 4 1.33mol), 24.8 grams of 3,3'-diaminodiphenyl disulfide (0.1mol), the temperature was raised to 200°C, and the reaction was kept for 10 hours.

[0058] After the reaction was completed, it was lowered to room temperature, 300 g of water was added, and a brown solid was precipitated. After suction filtration, the filter cake (brown solid) was washed once with 200ml of water. Put the washed filter cake into 300 g of 5% liquid caustic soda and heat up to 85° C. to dissolve, add 0.5 g of activated carbon and insulate and stir for 30 minutes. After suction filtration, about 42 grams of 36% hydrochloric acid (the pH value is about 3-4 at this time) was added dropwise to the filtrate, and a light brown powder was precipitated. After suction filtration, the filter cake (light brown powder) was dissolved with 150ml of isopropanol and heated to 80°C, ...

Embodiment 3、3

[0063] Embodiment 3,3, the synthesis of 3'-dimethoxy diphenyl disulfide

[0064] 200 grams of 55% H 2 SO 4 Aqueous solution (H 2 SO 4 1.12mol), 50 grams of methanol (1.56mol), 24.8 grams of 3,3'-diaminodiphenyl disulfide (0.1mol), the temperature was raised to 220°C, and the reaction was kept for 12 hours.

[0065] After the reaction was completed, it was lowered to room temperature, 300 g of water was added, and a brown solid was precipitated. After suction filtration, the filter cake (brown solid) was washed once with 200ml of water. Put the washed filter cake into 300 grams of 2% liquid caustic soda and heat it up to 85°C to dissolve it, add 0.5 grams of activated carbon and keep it warm for 30 minutes, and then suction filter while it is hot. The filter cake obtained by suction filtration is a brown solid, and the filter cake is heated with 200 grams of toluene After dissolving at 100°C, add 0.5 g of activated carbon and stir for 1 hour, then suction filter while it i...

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Abstract

The invention discloses a synthesis method of 3-substituent diphenyl sulfide, which comprises the following steps: synthesizing hydroxyl: adding a sulfuric acid solution with the mass concentration of 30-70% into a raw material, conducting heating to 130-250 DEG C, and conducting reacting for 4-20 hours; synthesizing alkoxy: adding a sulfuric acid solution with the mass concentration of 30-70% and an alcohol solvent into the raw materials, conducting heating to 130-250 DEG C, and conducting reacting for 4-20 hours; and carrying out post-treatment on the obtained reaction product to obtain the 3-substituent diphenyl sulfide. The method is simple in process and convenient to operate, and the dangerous process of diazotization is avoided.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, specifically a method for preparing the corresponding 3-hydroxy or 3-alkane in one step by hydrolysis or alcoholysis using 3-aminodiphenyl sulfide or 3,3'-diaminodiphenyl sulfide as raw material. Synthetic method of oxydiphenyl sulfide. Background technique [0002] 3-substituent diphenyl sulfide includes 3-hydroxy diphenyl sulfide and 3-alkoxy diphenyl sulfide, 3-hydroxy diphenyl sulfide and 3-alkoxy diphenyl sulfide are important fine chemical Products, are widely used in medicine, pesticides, materials, flavors and other fields. 3,3'-dihydroxydiphenyl disulfide and 3,3'-dimethoxydiphenyl disulfide can be reduced to obtain 3-methoxythiophenol and 3-hydroxythiophenol Intermediates, these two intermediates can be used in the synthesis of pharmaceuticals such as raloxifene and alevoxifen; 3,3'-dihydroxydiphenyl disulfide and 3,3'-dimethoxydiphenyl disulfide It is also used as an auxil...

Claims

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Application Information

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IPC IPC(8): C07C323/20C07C319/20C07C319/22
CPCC07C319/20C07C319/22C07C323/20
Inventor 葛前建陶晓敏朱航汤文杰陈佳玲张永彬李桂芹
Owner 江西扬帆新材料有限公司
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