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A kind of preparation method of aqueous phase sulfide compound and product thereof

A compound and phase thioether technology, applied in the field of preparation of thioether compounds, can solve problems such as strong toxicity, climate change, flammability and explosion

Inactive Publication Date: 2020-10-20
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As we all know, in the field of organic synthesis, the organic solvents used by people have serious problems such as strong toxicity, refractory degradation, flammability and explosion, and climate change. Therefore, the inevitable solvent pollution problem needs to be solved urgently, and a green and efficient sulfide is developed. The method of synthesis is critical

Method used

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  • A kind of preparation method of aqueous phase sulfide compound and product thereof
  • A kind of preparation method of aqueous phase sulfide compound and product thereof
  • A kind of preparation method of aqueous phase sulfide compound and product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]

[0044] In a pre-dried 4mL reaction bottle, at room temperature, sequentially add zinc dichloride (3.28mg, 0.024mmol), 1,3-dimethoxybenzene (32.0μL, 0.24mmol), surfactant TPGS-750- M aqueous phase system (0.4mL), stir the mixture evenly, add allylphenyl sulfide (35.2μL, 0.24mmol), slowly add periodiodine compound PIFA (105.2mg, 0.24mmol) and stir at 500rpm while heating to 60°C 24h.

[0045] After the reaction solution was stirred, it was extracted three times with ethyl acetate, and the organic phases extracted several times were combined into a 25mL eggplant-shaped flask, and the Heidolph rotary evaporator was used at a speed of 80-100rpm, a temperature of 38°C, and a vacuum of 0.1Mpa. , treated for 3 min, and then subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether: ethyl acetate = 49:1, and the target compound 1 was isolated. (41.3 mg, the yield is 70%, and the purity analyzed by HPLC is 98%....

Embodiment 2

[0049]

[0050] In a pre-dried 4mL reaction bottle, at room temperature, sequentially add zinc dichloride (3.28mg, 0.024mmol), 1,3-dimethoxybenzene (32.0μL, 0.24mmol), surfactant TPGS-750- M aqueous phase system (0.4mL), stir the mixture evenly, add 4-methoxyallyl phenyl sulfide (43.2mg, 0.24mmol), slowly add periodiodine compound PIFA (105.2mg, 0.24mmol) and heat to 60°C Stir at 500 rpm for 24 h at temperature.

[0051] After the reaction solution was stirred, it was extracted three times with ethyl acetate, and the organic phases extracted several times were combined into a 25mL eggplant-shaped flask, and the Heidolph rotary evaporator was used at a speed of 80-100rpm, a temperature of 38°C, and a vacuum of 0.1Mpa. , treated for 3 min, and then subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether: ethyl acetate = 49:1, and the target compound 2 was isolated. (34.5mg, productive rate is 52%, and the puri...

Embodiment 3

[0054]

[0055] In a pre-dried 4mL reaction bottle, at room temperature, sequentially add zinc dichloride (3.28mg, 0.024mmol), 1,3,5-trimethoxybenzene (41.2mg, 0.24mmol), surfactant TPGS-750 -M water phase system (0.4mL), the mixture was stirred evenly and added 4-methoxyallyl phenyl sulfide (43.2mg, 0.24mmol), slowly added periodiodine compound PIFA (105.2mg, 0.24mmol) and heated to 60 Stir at 500 rpm for 24 h at °C.

[0056] After the reaction solution was stirred, it was extracted three times with ethyl acetate, and the organic phases extracted several times were combined into a 25mL eggplant-shaped flask, and the Heidolph rotary evaporator was used at a speed of 80-100rpm, a temperature of 38°C, and a vacuum of 0.1Mpa. , treated for 3 min, and then subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether: ethyl acetate = 19:1, and the target compound 3 was isolated. (51.4 mg, the yield is 70%, and the pur...

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Abstract

The invention discloses a preparation method and products of a water phase thioether compound. The preparation method comprises following steps: ferric trichloride or zinc chloride are introduced intoa 4mL reaction bottle, an aryl compound and a water phase system containing 2wt.% surfactant TPGS-750-M are added at the same time, diallyl sulfide is added, stirring is carried out at a rotating speed of 500 to 1000rpm, 1min later, high iodine compound PIFA is added gradually, an obtained mixture is heated, and is stirred for 24 to 36h, ethyl acetate is adopted for extraction, rotary evaporationcondensation is carried out, and then silica gel column chromatography separation is adopted so as to obtain a product. The preparation method is capable of generating new C-S bonds from the simple aryl compound and the diallyl sulfide compound, low-toxicity high iodine salt reagent is adopted for catalysis, no metal catalyst or organic solvent system is needed, metal and solvent residue problemsare solved, operation is simple, yield is high, purity is 98% or higher, conditions are mild, substance range is wide, and the irritating odor of conventional thioether compound synthesis raw materials (thiophenol and mercaptan) is avoided.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of thioether compounds and products thereof. Background technique [0002] For the synthesis of aryl sulfides, at present, there are two mainstream synthesis methods: first, metal-catalyzed cross-coupling reaction; second, C-H activation. The cross-coupling reaction needs to be catalyzed by noble metals or transition metals, and pre-activated aryl halides are required. However, most of the C-H activation requires high reaction temperature and harsh reaction conditions, and its substrates are also limited by functional groups, so the applicability is poor. [0003] As early as 1991, the American Chemical Society proposed the concept of "green chemistry", and then put forward twelve principles of "green chemistry". As we all know, in the field of organic synthesis, the organic solvents used by people have serious problems such as strong toxicity, r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/20C07C323/37
CPCC07C319/14C07C323/20C07C323/37
Inventor 黄申林尹太玉冯庆源梁辉
Owner NANJING FORESTRY UNIV
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