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Synthesis method of silver(I) trifluoromethanethiolate

A trifluoromethane and synthesis method technology, which is applied in mercaptan preparation, organic chemistry, bulk chemical production, etc., can solve the problems of low utilization rate of silver atoms, high synthesis cost, and many wastes

Active Publication Date: 2021-05-11
SHANDONG LINGHAI BIOTECHNOLOGY CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Silver (I) trifluoromethanethiolate is an important nucleophilic trifluoromethyl sulfide reagent, which plays an important role in the trifluoromethyl sulfide reaction, but its original synthesis method has a low utilization rate of silver atoms, and the formation is relatively low. (Zheng HD, Huang YJ, Weng ZQ. Recent advances in triflfluoromethylthiolation using nucleophilic triflfluoromethylthiolating reagents [J]. Tetrahedron Letters, 2016, 57(13): 1397–1409; Zhang PP, Lu L, Shen, QL . Recent Progress on Direct Trifluoromethylthiolating Reagents and Methods [J]. Acta Chim. Sinica, 2017, 75, 744—769), resulting in higher synthesis costs and more waste

Method used

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  • Synthesis method of silver(I) trifluoromethanethiolate
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  • Synthesis method of silver(I) trifluoromethanethiolate

Examples

Experimental program
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Effect test

Embodiment 1

[0022]Example 1: In this example, silver fluoride (3a) (S- (Trifluoromethyl) [1,1'-Biphenyl] -4-Carbothioate) is used to synthesize trifluoride using fluorinated silver. Methane sil silver (I)

[0023]The reaction equation is:

[0024]

[0025]The synthesis steps and processes are: adding fluorinated silver (0.4 mmol, 51 mg) to 10 ml of reaction tubes equipped with magnetic stirrer, and triflicate 3a (1.0 mmol, 282 mg) of phenylbenzoate, and then 4.0 ml of dimethyl sulfoxide was added, and the reaction tube was immobilized on a magnetic stirrer, reacted at a 35 ° C oil bath for 24 hours, and purified to give a target product trifluoromethane silver (I), yield 67.8%.

Embodiment 2

[0026]Example 2: In this example, silver-soluble ferromethane silver (I) is reacted with ferride andtes trifluorometherane (3b) (S- (Trifluoromethyl) DodecaneThioate)

[0027]The reaction equation is:

[0028]

[0029]The synthesis steps and processes are: adding fluorinated silver (0.5 mmol, 63.5 mg), tetralate 3b (2.0 mmol, 568 mg), and then add 4.0 ml to the 10 ml reaction tube equipped with magnetic stirrer. 1.4-dioxane; fixing the reaction tube on the magnetic stirrer, at room temperature for 18 hours, separation and purification to obtain a target product trifluoromethane silver (I), yield 47.7%.

Embodiment 3

[0030]Example 3: In this example, silver fluorine thiol silver is synthesized by hydrofluorine and trifluoromethylfluoromethane (3c) (S- (Trifluoromethyl) 4- (Trifluoromethyl) Benzothioate) (I)

[0031]The reaction equation is:

[0032]

[0033]The synthesis steps and processes are: 1 ml, 1 mmol, 127 mg), which is added to a 10 ml reaction tube equipped with a magnetic stirrer, and trifluoromethyltromethane 3c (1.0 mmol, 274 mg) is added to trifluoromethylbenzoate. Further, 3.0 mL of acetonitrile was added, and the reaction tube was fixed on the magnetic stirrer, and after 15 degrees Celsius was completed for 36 hours, the separation was purified to obtain a target product trifluoromethane silver (I), yield 72.5%.

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Abstract

The invention belongs to the technical field of synthesis of organic compounds, and relates to a synthesis method of silver(I) trifluoromethanethiolate. According to the synthesis method of silver(I) trifluoromethanethiolate (CAS number: 811-68-7) in the invention, silver fluoride is used as a raw material and trifluoromethylthioester is used as a trifluoromethylthio source so as to synthesize silver(I) trifluoromethanethiolate. According to the method, trifluoromethylthioester is used as the trifluoromethylthio source and reacts with the silver fluoride in a solvent to generate silver(I) trifluoromethanethiolate, and a finished silver(I) trifluoromethanethiolate product is obtained after separation and purification. According to the synthesis method of silver(I) trifluoromethanethiolate, raw materials are easy to obtain, reaction reagents are easy to prepare and low in price, the synthesis cost of silver(I) trifluoromethanethiolate is remarkably reduced, synthesis conditions are mild, operation is easy, convenient and safe, industrial production is facilitated, the utilization rate of silver atoms is high, and environmental protection is realized.

Description

Technical field[0001]The present invention is a synthesis method of organic compound synthesis, and a synthetic method of trifluoromethane silver (I).Background technique[0002]The fluorine atom has an important position in modern drug design and synthesis (liu X, Xu C, WANG M, ETAL. Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation andbeyond [J]. Chem Rev, 2015, 115 (2): 683-730.), According to statistics, 15% to 20% of modern drugs contain a fluorine-containing group (Hui R, ZHANG S, TAN Z, ET Al. Research Progress oftrifloromethylation with sodium trifluoromethanesulfinate [J] .Chin J OrgChem (Organic Chemistry), 2017, 37 (12): 3060-3075). The presence of fluorine-containing groups helps to increase the lipophilic, metabolic stability of drug molecules (Yang B, Xu XH, QING FL. Copper-Mediated Radical 1, 2-Bis (Trifluoromethem) of Alkenes With Sodium Trifluoromethanesulfinate [J]. ORG Lett, 2015, 17 (8): 1906-1909.) Also reduces drug resistance. At the same time, tr...

Claims

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Application Information

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IPC IPC(8): C07C319/02C07C323/03
CPCC07C319/02C07C323/03Y02P20/55C07F1/10
Inventor 史大永田阳许凤
Owner SHANDONG LINGHAI BIOTECHNOLOGY CO LTD
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