CN117603107B - Perfluoro hydrocarbon thio silver reagent and preparation and application method thereof - Google Patents
Perfluoro hydrocarbon thio silver reagent and preparation and application method thereof Download PDFInfo
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Abstract
The invention discloses a perfluorocarbon sulfur-based silver reagent and a preparation and application method thereof, belonging to the field of organic chemistry. The intermediate thioperfluoro acetate is prepared by the reaction of (trifluoromethyl) trimethylsilane, cesium fluoride and carbon disulfide, and then the intermediate thioperfluoro acetate and silver fluoride are subjected to desulfurization and fluorination reaction, so that the perfluoroethylthio silver reagent is successfully obtained. The perfluoro-ethylthio-silver reagent is taken as a reactant and reacts with N-halogenated phthalimide compounds to obtain an electrophilic N-perfluoro-ethylthio-phthalimide reagent, the types of pentafluoroethylthio-reagent are enriched, and meanwhile, the perfluoro-ethylthio-silver reagent has potential application value in the fields of medicine research and development, organic synthesis, antibacterial coating and the like.
Description
Technical Field
The invention particularly relates to a perfluorocarbon sulfur-based silver reagent and a preparation and application method thereof, belonging to the field of organic chemistry.
Background
The fluorine-containing hydrocarbon sulfur group is introduced into organic molecules, so that the lipophilicity of the parent molecule can be improved, the absorptivity and metabolic stability of the parent molecule in organisms can be enhanced, and the fluorine-containing hydrocarbon sulfur group has high value in research and application of pharmaceutical chemistry. The number of drugs containing fluorocarbon thio-segments on the market is also rapidly increasing, driven by market demand. Therefore, attention and attention have been paid to a method for efficiently introducing a sulfur-containing fluorocarbon functional group into a parent structure, which has been an important point of research in organofluorine chemistry. In recent years, various fluorine-containing hydrocarbon thio reagents have been developed by researchers and applied to research on fluorine-containing hydrocarbon thio reactions of organic molecules, but the reagents are often limited to SCF 3 and SCF 2 H groups, and the preparation and reaction research of perfluoroethylthio reagents are reported. The design of efficient, convenient and economical fluorocarbon-containing thiolation reagents is of critical importance, and particularly the current rare pentafluoroethylthiolation reagents are in urgent need of research and development. Therefore, the design and synthesis of a novel pentafluoroethylthio reagent and the expansion of a corresponding pentafluoroethylthio reaction strategy have important research value and significance.
Disclosure of Invention
The invention develops a preparation method and application of a novel perfluorocarbon sulfur-based silver reagent, namely a perfluoroethylsulfur-based silver reagent and application thereof in synthesis of electrophilic N-perfluoroethylsulfur-based reagent and antibacterial paint. In the preparation method of the perfluoroethylthio silver, the invention obtains a sulfo-perfluorocesium acetate intermediate through the reaction of (trifluoromethyl) trimethylsilane, cesium fluoride and carbon disulfide, prepares the perfluoroethylthio silver compound through the reaction of sulfo-perfluorocesium acetate and silver fluoride, and synthesizes the N-perfluoroethylthio-phthalimide through the reaction of N-halogenated phthalimide and perfluoroethylthio silver in the synthesis method of an electrophilic N-perfluoroethylthio reagent. In addition, the inhibition of Staphylococcus aureus, escherichia coli and Klebsiella pneumoniae by perfluoroethylthio silver was examined.
The invention aims to provide perfluoroethylthio silver, which has a structural formula of AgSC 2F5.
The invention also provides a preparation method for preparing the perfluoroethylthio silver, which comprises the following steps:
(1) in an organic solvent, reacting (trifluoromethyl) trimethylsilane shown in the formula (1), cesium fluoride shown in the formula (2) and carbon disulfide shown in the formula (3) to obtain cesium thioperfluoroacetate (CF 3CS2 Cs) shown in the formula (4) after the reaction is finished;
(2) And (3) reacting the obtained cesium thioperfluoroacetate shown in the formula (4) with silver fluoride as a reactant, and obtaining the perfluoroethylthio silver shown in the formula (5) after the reaction is finished.
In one embodiment of the invention, the reaction of step (1) is carried out in an organic solvent environment, said organic solvent comprising any one or more of ethylene glycol dimethyl ether (DME), diethyl ether (Et 2 O), ethylene glycol diethyl ether, preferably DME.
In one embodiment of the invention, cesium fluoride is used in step (1) in an amount of 0.1 to 1.0mmol/mL relative to the organic solvent. Specifically, 0.4mmol/mL is optional.
In one embodiment of the invention, in step (1), the molar ratio of cesium fluoride to carbon disulfide is 1 (1.0-2.0). A specific preferred ratio is 1:1.8.
In one embodiment of the present invention, the molar ratio of cesium fluoride to (trifluoromethyl) trimethylsilane in step (1) is 1 (1.0-2.0). A specific preferred ratio is 1:1.5.
In one embodiment of the invention, the temperature of the reaction of step (1) is from-10 ℃ to 10 ℃. Preferably 0 ℃.
In one embodiment of the invention, the reaction time of step (1) is 3 to 8 hours. Preferably 6 hours.
In one embodiment of the invention, the reaction of step (1) is carried out in an inert atmosphere. Such as nitrogen.
In one embodiment of the invention, the molar ratio of the cesium thioperfluoroacetate salt to silver fluoride in step (2) is 1 (3.0-6.0). A specific preferred ratio is 1:3.3.
In one embodiment of the invention, the reaction of step (2) is carried out in a solvent which is any one or more of Tetrahydrofuran (THF), acetonitrile (MeCN). THF is preferred.
In one embodiment of the invention, the cesium thioperfluoroacetate salt of step (2) is used in an amount of 0.2 to 0.5mmol/mL relative to the solvent. Specifically, 0.36mmol/mL is optional.
In one embodiment of the invention, the temperature of the reaction of step (2) is from 70 ℃ to 90 ℃. Preferably 70 ℃.
In one embodiment of the invention, the reaction time of step (2) is from 6 to 24 hours. Specifically, the time is selected to be 14h.
In one embodiment of the invention, the reaction of step (2) is carried out in an inert atmosphere. Such as nitrogen.
The invention also provides application of the perfluoroethylthio silver in preparation of perfluoroethylthio phthalimide reagent.
In one embodiment of the present invention, a method for preparing a perfluoroethylthio phthalimide reagent comprises the following steps:
In a solvent, reacting N-halogenated phthalimide shown in a formula (6) with perfluoroethyl silver sulfide shown in a formula (5) as reactants to obtain an N-perfluoroethylthio phthalimide reagent shown in a formula (7);
Wherein X is selected from Cl and Br, and the formula (7) is N-perfluoroethylthio phthalimide or N-perfluoroethylthio hexahydrophthalimide.
In one embodiment of the present invention, the reaction is carried out in a solvent comprising one or more of acetonitrile (MeCN), tetrahydrofuran (THF), preferably MeCN, when synthesizing the N-perfluoroethylthio phthalimide reagent of formula (7).
In one embodiment of the present invention, the molar ratio of the N-halophthalimide to the perfluoroethylsilver sulfide is 1 (1.0-2.0). Preferably 1:1.1.
In one embodiment of the invention, the N-halophthalimide is used in an amount of 0.1 to 1.0mmol/mL relative to the solvent. Specifically, 0.4mmol/mL is optional.
In one embodiment of the present invention, the reaction temperature is 20 ℃ to 50 ℃ when synthesizing the N-perfluoroethylthio-phthalimide reagent represented by formula (7). Room temperature (20-30 ℃) is preferred.
In one embodiment of the present invention, the reaction time is 2 to 8 hours when synthesizing the N-perfluoroethylthio phthalimide reagent represented by formula (7). Preferably 4 hours.
In one embodiment of the invention, a novel green and economical preparation method of perfluoroethyl silver sulfide comprises the following steps:
Taking (trifluoromethyl) trimethylsilane, cesium fluoride and carbon disulfide as raw materials, stirring and reacting for a period of time in a nitrogen (N 2) atmosphere at-10 ℃ to obtain a crude product of the cesium thio-perfluoro acetate, filtering, washing and distilling under reduced pressure to obtain the cesium thio-perfluoro acetate, stirring and reacting for a period of time in a nitrogen (N 2) atmosphere at 70 ℃ to 90 ℃ to obtain a crude product of the perfluoroethylthio-silver, and filtering, washing and distilling under reduced pressure to obtain the perfluoroethylthio-silver.
In one embodiment of the invention, the method is preferably carried out by adding (trifluoromethyl) trimethylsilane, cesium fluoride and carbon disulfide into a reaction vessel containing ethylene glycol dimethyl ether solvent according to a molar ratio of 1.5:1:1.8 under the condition of keeping nitrogen atmosphere, stirring for 3-8 hours at-10 ℃ and 10 ℃, and separating and purifying to obtain the cesium salt of thioperfluoroacetate intermediate. Adding cesium thioperfluoroacetate and silver fluoride into a reaction vessel containing tetrahydrofuran solvent according to a molar ratio of 1:3.3, stirring for 12-24 hours at 70-90 ℃, and separating the purified perfluoroethylthio silver reagent.
In one embodiment of the invention, the method for synthesizing N-perfluoroethylthio phthalimide comprises the following steps:
n-halogenated phthalimide and perfluoroethylthio silver are used as raw materials, the raw materials are stirred and reacted for a period of time at 20-50 ℃ in nitrogen (N 2) atmosphere to obtain the crude product of the N-perfluoroethylthio phthalimide reagent, and then the pure product is obtained through filtration, washing, extraction and reduced pressure distillation.
In one embodiment of the invention, the method is preferably carried out by adding N-halogenated phthalimide and perfluoroethylthio silver into a reaction vessel containing acetonitrile solvent according to a molar ratio of 1:1.1 under the atmosphere of nitrogen, stirring for 2-8 hours at 20-50 ℃, and separating and purifying to obtain the pure N-perfluoroethylthio phthalimide reagent.
In one embodiment of the invention, the resulting N-perfluoroethylthio-phthalimide can be used as a reagent for perfluoroethylthioetherification of a variety of biologically active molecules. Such as described in prior document (Electrophilic Reagents for the Direct Incorporation of Uncommon SCF2CF2H and SCF2CF3Motifs.J.Org.Chem.2022,87,10791-10806).
The invention also provides application of the perfluoro ethyl silver sulfide in preparation of a bacteriostatic agent.
The invention also provides a bacteriostatic agent containing the perfluoroethyl silver sulfide.
The invention provides application of the perfluoro ethyl silver sulfide in the bacteriostasis field of diagnosis and treatment of non-diseases.
Advantageous effects
In the method, (trifluoromethyl) trimethylsilane, cesium fluoride and carbon disulfide are reacted in a nitrogen atmosphere to obtain a sulfo-perfluoro cesium acetate intermediate, the sulfo-perfluoro cesium acetate reacts with silver fluoride to prepare a perfluoro ethylthio silver reagent, and the perfluoro ethylthio silver reacts with N-halogeno-phthalimide to generate the N-perfluoro ethylthio-phthalimide reagent, so that the types of pentafluoroethylthio reagent are enriched.
The target compound of the method has potential application value in the fields of medicine research and development, organic synthesis, antibacterial coating and the like.
Drawings
FIG. 1 is a synthetic scheme for the perfluorocarbon thio silver reagent of the present invention.
FIG. 2 is a synthetic scheme of N-perfluoroethylthio-phthalimide reagent of the present invention.
Detailed Description
The following is a specific embodiment of the perfluoroethyl silver sulfide according to the present invention.
The synthetic route diagram of the embodiment of the invention is shown in fig. 1:
Adding (trifluoromethyl) trimethylsilane, cesium fluoride and carbon disulfide serving as raw materials into a reaction bottle containing ethylene glycol dimethyl ether under the nitrogen atmosphere, then placing the reaction bottle into an ice bath kettle at the temperature of-10 ℃ to 10 ℃ for fully reacting for 3-8 hours to obtain a crude product of the cesium thioperfluoroacetate, separating and purifying, adding the cesium thioperfluoroacetate and silver fluoride serving as raw materials into the reaction bottle containing acetonitrile under the nitrogen atmosphere, and then placing the reaction bottle into an oil bath kettle at the temperature of 70 ℃ to 90 ℃ for fully reacting for 12-24 hours.
EXAMPLE 1 preparation of perfluoroethylthio silver
(1) Cesium fluoride 1.52g (10.0 mmol,1.0 equiv) was weighed into a 50mL Schlemk reaction flask, 25mL anhydrous ethylene glycol dimethyl ether (DME) and carbon disulfide 1.37g (18.0 mmol,1.8 equiv) were added under the protection of nitrogen at 0℃and stirred for 5 minutes, TMSCF 3 (2.13 g,15.0mmol,1.5 equiv) was slowly added dropwise by syringe, and after the addition was completed, the reaction was continued at 0℃for 3 hours. The solution color slowly deepens (eventually, a dark red color) as the reaction proceeds. After the reaction, diluting the reaction solution with ethyl acetate, filtering to remove unreacted CsF, distilling under reduced pressure to remove the solvent, adding petroleum ether to precipitate solid, collecting filter residues, and drying to obtain an orange solid intermediate CF 3CS2 Cs cesium salt (2.23 g, yield 80%);
(2) 2.00g (7.2 mmol,1.0 equiv) of the resulting CF 3CS2 Cs cesium salt and 3.0g (23.7 mmol,3.3 equiv) of silver fluoride were weighed separately, charged into a 50mL three-necked flask, 20mL of dry THF was added under nitrogen protection, and the reaction was completed after refluxing at 70℃for 14 hours. The solvent was distilled off under reduced pressure, ethyl acetate (20 mL) was added, the mixture was filtered with celite, the filtrate was collected, the solvent was distilled off under reduced pressure, a small amount of acetonitrile was added to dissolve the solid, and then a proper amount of petroleum ether was added along the wall of the flask to recrystallize to obtain a large amount of solid, which was filtered, the filter residue was collected and dried to obtain yellow solid AgSC 2F5 1.64.64 g in 80% yield.
19F NMR(376MHz,DMSO-d6)δ-63.46(q,J=5.5Hz,2F),-82.51(t,J=5.5Hz,3F).
EXAMPLE 2 Effect of different solvents on the preparation of cesium thioperfluoroacetate
Referring to example 1, the solvent in step (1) was adjusted, and the other was unchanged, to prepare the corresponding product. The results are shown in Table 1.
TABLE 1 Effect of different solvents on the preparation of cesium thioperfluoroacetate salts
| Solvent(s) | Yield (%) a |
| DME | 80 |
| Ethylene glycol diethyl ether | 74 |
| Diethyl ether | 43 |
| H2O | 0 |
A. yield is isolated yield
As a result, it was found that the use of ethylene glycol diethyl ether, water instead of ethylene glycol dimethyl ether in example 1 as a solvent gave a product having a lower yield than that of example 1.
EXAMPLE 3 Effect of different temperatures on the preparation of cesium thioperfluoroacetate
Referring to example 1, the temperature in step (1) was adjusted, and the corresponding product was prepared without change. The results are shown in Table 2.
TABLE 2 Effect of different temperatures on the preparation of cesium thioperfluoroacetate salts
| Temperature (° C) | Yield (%) a |
| -10 | 70 |
| 0 | 80 |
| 10 | 67 |
A. yield is isolated yield
As a result, it was found that the product yields obtained by substituting-10℃and 10℃for 0℃in example 1 were inferior to those obtained in example 1.
EXAMPLE 4 Effect of different solvents on the preparation of silver perfluoroethylthio
Referring to example 1, the solvent in step (2) was adjusted, and the other was unchanged, to prepare the corresponding product. The results are shown in Table 3.
TABLE 3 Effect of different solvents on the preparation of perfluoroethyl silver sulfide
| Solvent(s) | Yield (%) a |
| THF | 80 |
| MeCN | 64 |
A. yield is isolated yield
As a result, it was found that the use of acetonitrile in place of tetrahydrofuran in example 1 as a solvent gave a product having a lower yield than example 1.
EXAMPLE 5 Effect of different temperatures on the preparation of silver perfluoroethylthio
Referring to example 1, the temperature in step (2) was adjusted, and the corresponding product was prepared without change. The results are shown in Table 4.
TABLE 4 influence of different temperatures on the preparation of cesium thioperfluoroacetate salts
| Temperature (° C) | Yield (%) a |
| 70 | 80 |
| 80 | 79 |
| 90 | 76 |
A. yield is isolated yield
As a result, it was found that the product yields obtained by substituting 80℃and 90℃for 70℃in example 1 were inferior to those obtained in example 1.
Example 6 antibacterial Property detection of silver perfluoroethylthio
100G of steel plate finishing paint is taken, added with 0.5g AgSC 2F5 and stirred at a high speed for one hour to prepare the antibacterial paint. Then, on the primed steel sheet, an antimicrobial coating was applied using an RDS #16 bar and baked for 55 seconds with a 260℃air oven to form a 15 μm steel sheet topcoat coating, thereby preparing an evaluation template. A total of 19 test plates for evaluation were prepared, and a third party detection mechanism was commissioned, and the test was conducted on the test plates for evaluation according to JIS Z2801:2010amendment & 2012 "antibacterial processed product-antibacterial Activity and effectiveness test", and the test results showed that the antibacterial Activity against Staphylococcus aureus was 5.7, the antibacterial Activity against Escherichia coli was 6.5, and the antibacterial Activity against Klebsiella pneumoniae was 6.3. The activity values are converted into antibacterial rate, and the antibacterial rate of AgSC 2F5 to above three bacteria of staphylococcus aureus, escherichia coli and klebsiella pneumoniae is above 99.9%.
Performance comparison of the known similar structures, comparison of antibacterial effects against staphylococcus aureus, escherichia coli, with reference to the antibacterial test procedure described above. As a result of replacing AgSC 2F5 with AgSCF 3 having the same mass, it was found that AgSCF 3 had an antibacterial activity value of 0.7 against Staphylococcus aureus, 1.2 against Escherichia coli, and 80.00% and 93.32 against Staphylococcus aureus and Escherichia coli, respectively, which were remarkably inferior to AgSC 2F5, as converted into antibacterial ratios.
EXAMPLE 7 Synthesis of aryl perfluoroethyl sulfide Using perfluoroethylthio silver
4-Nitrophenyl tetrafluoroborate diazonium salt (118 mg,0.5 mmol), agSC 2F5 (194 mg,0.75 mmol), cuprous iodide (95 mg,0.5 mmol), potassium carbonate (138 mg,1.0 mmol) and acetonitrile (5 mL) were added separately to a 50mL reaction tube equipped with a stirrer under room temperature air conditions, and stirred well at room temperature for 12 hours. After the completion of the reaction, the mixture after the reaction was diluted with methylene chloride, filtered through celite, and washed with methylene chloride. The organic phases were combined, dried over anhydrous MgS 2O4, filtered, the filtrate was added with a small amount of silica gel, concentrated in vacuo, and the target was purified by column chromatography using n-hexane/ethyl acetate as eluent to give 95mg of the product in 70% yield.
1H NMR(400MHz,CDCl3)δ8.28(d,J＝8.9Hz,2H),7.85(d,J＝8.8Hz,2H).19F NMR(376MHz,CDCl3)δ-82.53(t,J＝3.4Hz,3F),-90.83(q,J＝3.4Hz,2F).13C NMR(101MHz,CDCl3)δ149.6(s),137.6(s),131.0(t,J＝2.6Hz),124.4(s),120.1(tq,J＝291.0,41.0Hz),118.6(qt,J＝286.7,36.2Hz).
The prior report (Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides.Russ.Chem.Bull.,Int.Ed.,Vol.53,No.2,February,2004) discloses a method for constructing aryl ethyl sulfide, which comprises the following steps:
The specific preparation process is that XeF 2 (1.4 g,8.2 mmol), peracetic acid (1.5 mL), 1, 2-bis (4-nitrophenyl) dithio (832 mg,2.7 mmol) and methylene chloride (30 mL) are added into a reaction tube at-20 ℃, stirred for reaction and naturally heated to 5 ℃. Neutralizing with Na 2CO3 aqueous solution, extracting with chloroform, drying the extract with Na 2SO4, distilling under reduced pressure to remove solvent, and separating and purifying the crude product by column chromatography with petroleum ether as eluent to obtain the target compound with a yield of 30.3%.
The corresponding preparation result is that the yield of the 4-nitrophenyl perfluoroethyl sulfide compound obtained by the method is only 30.3 percent, which is obviously lower than the yield (70 percent) of the method.
The following is a specific embodiment of the preparation of N-perfluoroethylthio-phthalimide reagent of the present invention.
The preparation route diagram of the embodiment of the invention is shown in fig. 1:
N-halogeno-phthalimide and perfluoroethylthio silver are taken as raw materials, the raw materials are added into a reaction bottle containing acetonitrile under the nitrogen atmosphere, and then the reaction bottle is placed into an oil bath pot with the temperature of 20 ℃ to 50 ℃ for full reaction for 2 to 8 hours.
EXAMPLE 8 Synthesis of N-perfluoroethylthio-phthalimide
1.81G (10.0 mmol,1.0 equiv) of N-chlorophthalimide and 2.85g (10.0 mmol,1.0 equiv) of perfluoroethylthio silver were weighed into a 50mL Schlemk reaction flask and 25mL anhydrous acetonitrile was added under nitrogen. After stirring at room temperature (25 ℃) for 4 hours, acetonitrile was distilled off under reduced pressure, ethyl acetate (20 ml) was added, the filtrate was collected, the solvent was distilled off under reduced pressure, and the remaining solid was further dried under vacuum to give 2.1g of a white solid in a yield of 70%.
1H NMR(400MHz,CDCl3)δ8.06–7.97(m,2H),7.91–7.83(m,2H).19F NMR(376MHz,CDCl3)δ-82.82(t,J＝3.1Hz,3F),-98.58(q,J＝2.8Hz,2F).13C NMR(101MHz,CDCl3)δ165.9(s),135.6(s),131.6(s),124.8(s),118.6(tq,J＝293.1Hz,41.4Hz),118.2(qt,J＝284.6Hz,36.0Hz).HRMS(ESI)m/z calculated for C10H5F5NO2S[M+H]+:297.9961,found 297.9956.
EXAMPLE 9N-perfluoroethylthio hexa Synthesis of hydro phthalimides
1.81G (10.0 mmol,1.0 equiv) of N-perfluoroethylthiohexahydrophthalimide and 2.85g (10.0 mmol,1.0 equiv) of perfluoroethylthiosilver were weighed into a 50mL Schlemk reaction flask and 25mL anhydrous acetonitrile was added under nitrogen. After stirring at room temperature for 4 hours, acetonitrile was distilled off under reduced pressure, ethyl acetate (20 ml) was added, and the filtrate was collected, the solvent was distilled off under reduced pressure, and the remaining solid was further dried under vacuum to give 2.1g of a white solid with a yield of 61%.
1H NMR(400MHz,CDCl3)δ3.07(td,J＝4.4,2.3Hz,1H),2.91(tt,J＝4.6,2.1Hz,1H),1.98–1.72(m,4H),1.47(tq,J＝9.1,4.6,4.0Hz,4H).19F NMR(376MHz,CDCl3)δ-82.97(t,J＝3.4Hz),-98.05(q,J＝3.3Hz).13C NMR(101MHz,CDCl3)δ180.04–179.92,177.07–176.88,122.70–121.24(m),120.13–118.25(m),117.32–115.76(m),41.24–40.74(d,J＝29.4Hz),24.37–23.70(d,J＝42.6Hz),22.18–21.74(d,J＝23.1Hz).HRMS(ESI)m/z calculated for C10H11F5N1O2S[M+H]+:304.0434,found:304.0431.
EXAMPLE 10 Effect of different solvents on the Synthesis of N-perfluoroethylthio-phthalimide
Referring to example 8, the types of solvents were adjusted, and the corresponding preparation results are shown in Table 5.
TABLE 5 influence of different solvents on the synthesis of cesium thioperfluoroacetate
| Solvent(s) | Yield (%) a |
| Acetonitrile | 70 |
| THF | 57 |
A. yield is isolated yield
As a result, it was found that the use of tetrahydrofuran in place of acetonitrile in example 8 as a solvent gave a product having a lower yield than that of example 8.
EXAMPLE 11 Effect of different temperatures on the Synthesis of N-perfluoroethylthio-phthalimide
Referring to example 8, the temperature was adjusted, and the other was unchanged, and the corresponding preparation results are shown in table 6.
TABLE 6 influence of different temperatures on the synthesis of cesium thioperfluoroacetate salts
| Temperature (° C) | Yield (%) a |
| 0 | 34 |
| 25 | 70 |
| 50 | 51 |
A. yield is isolated yield
As a result, it was found that the product yields obtained by substituting 0℃and 50℃for 25℃in example 8 were inferior to those obtained in example 8.
The above examples are not intended to limit the scope of the invention nor the order of execution of the steps described. The present invention is obviously modified by a person skilled in the art in combination with the prior common general knowledge, and falls within the scope of protection defined by the claims of the present invention.
Claims (5)
1. The preparation method of the perfluoroethylthio silver is characterized in that the structural formula of the perfluoroethylthio silver is AgSC 2F5, and the preparation method comprises the following steps:
(1) in an organic solvent, reacting (trifluoromethyl) trimethylsilane shown in the formula (1), cesium fluoride shown in the formula (2) and carbon disulfide shown in the formula (3) to obtain cesium thioperfluoroacetate (CF 3CS2 Cs) shown in the formula (4) after the reaction is finished;
(2) And (3) reacting the obtained cesium thioperfluoroacetate shown in the formula (4) with silver fluoride as a reactant, and obtaining the perfluoroethylthio silver shown in the formula (5) after the reaction is finished.
2. The method of claim 1, wherein the reaction of step (1) is performed in an organic solvent environment, the organic solvent comprising any one or more of ethylene glycol dimethyl ether, diethyl ether, and ethylene glycol diethyl ether.
3. The method according to claim 1, wherein cesium fluoride is used in the amount of 0.1 to 1.0 mmol/mL relative to the organic solvent in the step (1), the molar ratio of cesium fluoride to carbon disulfide is 1 (1.0 to 2.0), and the molar ratio of cesium fluoride to (trifluoromethyl) trimethylsilane is 1 (1.0 to 2.0).
4. The method according to claim 1, wherein the reaction in step (2) is carried out in a solvent, and the solvent is any one or more of tetrahydrofuran and acetonitrile.
5. The method of claim 4, wherein the cesium thioperfluoroacetate salt is used in step (2) in an amount of 0.2 to 0.5 mmol/mL relative to the solvent, and the molar ratio of cesium thioperfluoroacetate salt to silver fluoride is 1 (3.0 to 6.0).
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