CN111269152A - Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide - Google Patents
Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide Download PDFInfo
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- CN111269152A CN111269152A CN202010118586.7A CN202010118586A CN111269152A CN 111269152 A CN111269152 A CN 111269152A CN 202010118586 A CN202010118586 A CN 202010118586A CN 111269152 A CN111269152 A CN 111269152A
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- C07—ORGANIC CHEMISTRY
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
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Abstract
The invention discloses a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide, which comprises the steps of adopting trifluoromethanesulfonyl fluoride as a raw material, reacting organic base serving as an acid-binding agent with aniline in a strong polar solvent to generate N-phenyl trifluoromethanesulfonyl amide, distilling most of the solvent to remove, adding a weak polar solvent and a catalyst, and continuing to perform trifluoromethanesulfonyl fluoride reaction to obtain the N-phenyl bis (trifluoromethanesulfonyl) imide. The method has the advantages of low cost, mild reaction, no need of protective gas, no pollution caused by excessive emission of trifluoromethanesulfonyl fluoride, high purity of the prepared product, high yield and capability of realizing industrial popularization.
Description
Technical Field
The invention belongs to the field of fine chemical engineering, and particularly relates to a preparation method of N-phenyl bis (trifluoromethanesulfonimide).
Background
N-phenyl bis (trifluoromethanesulfonyl) imide is a highly efficient trifluoromethanesulfonylation reagent and can be used for trifluoromethanesulfonylation of enols, phenols and amines without reaction with alcohols. Therefore, the method is widely applied to the synthesis of medical intermediates and material intermediates. And is used for synthesizing the anti-prostate cancer drug abiraterone.
The synthetic route of N-phenyl bis (trifluoromethanesulphonimide) has so far been the following three:
Scheme 1：
Scheme 2：
various patents and literature reports on Scheme 1. For example, patents CN106518759, CN103717214CN102250065, CN105979779, JP2003286244, US20110230495, WO2015112441, WO2016027284, Tetrahedron Letters,46,4607-. This method has the following key problems: 1) the price of the raw material trifluoromethanesulfonic anhydride is high, and at least 2eq is used, so the production cost is high; 2) the reaction system has violent early stage of heat release, and the trifluoromethanesulfonic anhydride needs to be dropwise added at low temperature; 3) the reaction product has more impurities and low product purity, so that the product purity is low and the yield can reach 86 percent to the maximum; in order to achieve a yield of 90% or more, three conditions must be satisfied: inert gas protection, low-temperature control and slow dripping (JP 2003286244).
For Scheme 2, CN105693477 reports that trifluoromethanesulfonic acid is used as a raw material, dichlorosulfoxide is slowly dripped into a dichloromethane solution of trifluoromethanesulfonic acid to react to prepare trifluoromethanesulfonic chloride, and then the trifluoromethanesulfonic chloride is slowly dripped into a dichloromethane solution of aniline and triethylamine at a low temperature to prepare N-phenyl bis (trifluoromethanesulfonimide). The key problems of this method are: 1) the price of the raw material trifluoromethanesulfonic acid is expensive, so the production cost is high; 2) in the two-step reaction, the reaction progress is controlled by slowly dripping to prevent the danger of too much heat accumulation and material flushing; 3) thionyl chloride is also used in the first step of the reaction, and concentration is needed after acyl chloride is generated in the reaction, which can generate irritant acid mist and cause harm to surrounding operators and environment.
With respect to Scheme 3, Journal of Organic Chemistry,72(18),6758-6762,2007, a method for preparing N-phenyl bis (trifluoromethanesulfonyl) imide under nitrogen protection from an ionic liquid of diazobenzene tetrafluoroborate and 3- (1, 1-dimethylethyl) -1-methyl-1H-imidazolium bis (trifluoromethanesulfonyl) imide is reported. The key problems of this method are: 1) the ionic liquid of the 3- (1, 1-dimethylethyl) -1-methyl-1H-imidazolium bis (trifluoromethanesulfonyl) imide salt is not available on the market, and the ionic liquid is difficult to prepare, not only has high cost, but also is difficult to industrially prepare; 2) the method needs to be carried out under the protection of nitrogen, and the conditions are relatively harsh.
Disclosure of Invention
In order to solve the technical problem, the invention provides a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide, wherein trifluoromethanesulfonic anhydride is prepared by hydrolyzing and acidolyzing trifluoromethanesulfonyl fluoride, and then dehydrating phosphorus pentoxide; thus, if one could replace them with triflic anhydride and the starting triflyl fluoride from triflic acid production, the production cost of N-phenyl bis-triflimide would be greatly reduced.
The technical scheme adopted by the invention is as follows: a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide comprises the steps of taking trifluoromethanesulfonyl fluoride as a raw material, reacting organic base serving as an acid-binding agent with aniline in a strong polar solvent to generate N-phenyl trifluoromethanesulfonyl amide, and reacting the N-phenyl trifluoromethanesulfonyl amide with trifluoromethanesulfonyl fluoride in a weak polar solvent to obtain the N-phenyl bis (trifluoromethanesulfonyl) imide.
Preferably, the specific steps are as follows:
adding organic base serving as an acid-binding agent into a polar solvent, adding aniline, and introducing excessive trifluoromethanesulfonyl fluoride to prepare N-phenyltrifluoromethanesulfonamide;
distilling to remove the polar solvent, adding the weak polar solvent and the catalyst, and introducing excessive trifluoromethanesulfonyl fluoride to obtain a crude product of the N-phenyl bis (trifluoromethanesulfonyl) imide;
distilling to remove the weak polar solvent, and washing with an alcohol solvent to obtain a refined N-phenyl bis (trifluoromethanesulfonyl) imide;
preferably, the molar ratio of trifluoromethanesulfonyl fluoride to aniline is 1.1-5: 1;
preferably, the molar ratio of organic base to aniline is 2-4: 1;
preferably, the molar ratio of catalyst to aniline is 0.005-0.2: 1.
Preferably, in step two and step three, the excess of trifluoromethane sulfonyl fluoride is recovered before the polar or weakly polar solvent is recovered.
Preferably, the organic base is one of triethylenediamine, hexamethylenetetramine, 1, 8-diazabicycloundecen-7-ene (DBU).
Preferably, the catalyst is 4-dimethylaminopyridine or 4-pyrrolylpyridine.
Preferably, the polar solvent is a mixture of one or more of acetonitrile, N-dimethylformamide, N-dimethylacetamide, nitromethane, chlorobenzene, 1, 2-dichloroethane, chloroform, carbon tetrachloride, acetone, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether and ethylene glycol diethyl ether;
preferably, the polar solvent is acetonitrile, N-dimethylformamide or N, N-dimethylacetamide.
Preferably, the weakly polar solvent is a mixture of one or more of dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, toluene, benzene and tetrahydrofuran.
Preferably, the alcoholic solvent is a mixture of one or more of methanol, ethanol, isopropanol.
Preferably, the reaction temperature in the first step is 0-80 ℃, and the reaction temperature in the second step is-20-80 ℃;
preferably, the reaction temperature in the first step is 40-80 ℃ and the reaction temperature in the second step is 20-80 ℃.
Preferably, the mass ratio of the alcohol solvent to the crude product of the N-phenyl bis (trifluoromethyl) sulfimide is 0.5-5:1
The invention has the advantages and positive effects that:
according to the scheme, the trifluoromethanesulfonyl fluoride is used as a raw material, so that the production cost is obviously reduced; the reaction is mild, namely low-temperature cooling and inert gas protection are not needed, the method is suitable for industrial production, and the production environment is mild;
although the scheme is distributed, the intermediate product does not need to be purified, the operation process is simple, the crude product prepared by the method has higher purity and lighter color, the product can be purified by simple washing, and the purity is over 99 percent;
the excessive trifluoromethanesulfonyl fluoride can be circulated in the pipeline, cannot volatilize into the air, cannot be quenched into wastewater, can be recycled, and cannot cause environmental pollution.
Detailed Description
The following description is made of embodiments of the present invention.
The invention relates to a method for preparing N-phenyl bis (trifluoromethanesulfonyl) imide through stepwise reaction, which comprises the steps of activating trifluoromethanesulfonyl fluoride by using organic base to prepare N-phenyl trifluoromethanesulfonyl amide with high yield, and further activating the trifluoromethanesulfonyl fluoride by using a catalytic method to finally prepare the N-phenyl bis (trifluoromethanesulfonyl) imide. The N-phenyl bis (trifluoromethanesulfonyl) imide is prepared by reacting trifluoromethanesulfonyl fluoride serving as a raw material with aniline in a strong polar solvent by using an organic base as an acid-binding agent to generate N-phenyl trifluoromethanesulfonyl amide, and then reacting the N-phenyl trifluoromethanesulfonyl amide with trifluoromethanesulfonyl fluoride in a weak polar solvent.
The specific operation steps are as follows:
adding organic base serving as an acid-binding agent into a polar solvent, adding aniline, introducing excessive trifluoromethanesulfonyl fluoride, controlling the reaction temperature to be 0-80 ℃, and preparing N-phenyl trifluoromethanesulfonamide, wherein the molar ratio of the organic base to the aniline is 2-4: 1; preferably, the reaction temperature can be controlled to be 40-80 ℃;
recovering excessive trifluoromethanesulfonyl fluoride, distilling to remove the polar solvent, adding the weak polar solvent and the catalyst, controlling the reaction temperature to be-20-80 ℃, controlling the molar ratio of the catalyst to the aniline to be 0.005-0.2:1, and introducing the excessive trifluoromethanesulfonyl fluoride to prepare a crude product of the N-phenyl bis (trifluoromethanesulfonyl) imide, wherein the molar ratio of the trifluoromethanesulfonyl fluoride to the aniline introduced in the two steps is 1.1-5: 1; the reaction temperature can be controlled to be 20-80 ℃;
and step three, recovering excessive trifluoromethanesulfonyl fluoride, distilling to remove the weak polar solvent, washing with an alcohol solvent to obtain a refined N-phenyl bis (trifluoromethanesulfonyl) imide product, wherein the mass ratio of the alcohol solvent to the crude N-phenyl bis (trifluoromethanesulfonyl) imide is 0.5-5: 1.
Wherein the organic base is one of triethylene diamine, hexamethylene tetramine and 1, 8-diazabicycloundecen-7-ene (DBU).
Wherein the catalyst is 4-dimethylamino pyridine or 4-pyrrolyl pyridine.
Wherein the polar solvent is one or more of acetonitrile, N-dimethylformamide, N-dimethylacetamide, nitromethane, chlorobenzene, 1, 2-dichloroethane, chloroform, carbon tetrachloride, acetone, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether and ethylene glycol diethyl ether;
wherein the weak polar solvent is one or more of dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, toluene, benzene and tetrahydrofuran.
Wherein the alcohol solvent is one or more of methanol, ethanol and isopropanol.
During operation, aniline, organic base and solvent are added into a stainless steel reaction kettle, a trifluoromethanesulfonyl fluoride steel cylinder is connected, air in the reaction kettle is pumped out in vacuum, a certain amount of gaseous trifluoromethanesulfonyl fluoride is introduced until the reaction lasts for the theoretical time, and then the excessive trifluoromethanesulfonyl fluoride is discharged into a recovery tank through a pipeline and can be used for being introduced again for use; distilling most of the solvent in the reaction kettle to remove, adding the weak-polarity solvent and the catalyst, continuously introducing a certain amount of trifluoromethanesulfonyl fluoride gas, continuously reacting for a theoretical period of time, recovering excessive acyl fluoride, distilling to remove most of the solvent, adding the alcohol solvent, uniformly stirring, transferring the mixed solution into a filter, and filtering to obtain a white crystal which is the refined N-phenyl bis-trifluoromethanesulfonyl imide.
The present solution is further illustrated by the following specific examples.
Example 1:
adding 9.3 kg of aniline, 40L of acetonitrile and 13 kg of triethylene diamine into a 100L stainless steel reaction kettle, and connecting a trifluoromethanesulfonyl fluoride steel cylinder; evacuating the reaction kettle to-0.09 Mpa, introducing 20 kg of trifluoromethanesulfonyl fluoride gas, and sealing the reaction kettle; the reaction was stirred at 40 ℃ for 8 hours and the pressure in the reactor was observed to gradually decrease from 0.23MPa to 0.08MPa and remained unchanged for half an hour.
Opening the acyl fluoride recovery pipeline, recovering excessive acyl fluoride, and closing the acyl fluoride recovery pipeline after the pressure of the reaction kettle is reduced to 0 Mpa. The distillation system was opened and 34L of acetonitrile was distilled off. Then 40L of dichloromethane and 0.4 kg of 4-dimethylaminopyridine are added into the reaction kettle, 20 kg of trifluoromethanesulfonyl fluoride is introduced again, the reaction is sealed for 15 hours, and the pressure of the reaction kettle is reduced from 0.21Mpa to 0.06 Mpa.
Recovering excessive trifluoromethanesulfonyl fluoride, distilling to remove 38L of solvent to obtain yellow viscous solid, adding 30 kg of ethanol, quickly stirring, filtering to obtain white crystals, and drying to obtain 33.6 kg of refined N-phenyl bis (trifluoromethanesulfonyl) imide, wherein the detected purity is 99.2% and the yield is 94.0%.
Example 2
9.3 kg of aniline, 35L of dimethylformamide and 33 kg of DBU are added into a 100L stainless steel reaction kettle, and a trifluoromethanesulfonyl fluoride steel cylinder is connected. The reaction kettle is pumped to-0.09 Mpa, 22 kg of trifluoromethanesulfonyl fluoride gas is introduced, and the reaction kettle is sealed. Stirring and reacting for 8 hours at the temperature of 60 ℃, and gradually reducing the pressure of the reaction kettle from 0.29Mpa to 0.09Mpa without obvious change in half an hour. And opening the acyl fluoride recovery pipeline, recovering the excessive acyl fluoride, and closing the acyl fluoride recovery pipeline after the pressure of the reaction kettle is reduced to 0 Mpa. The distillation system was opened and 30L of dimethylformamide was distilled off. Then adding 50L of toluene and 0.3 kg of 4-dimethylaminopyridine, introducing 25 kg of trifluoromethanesulfonyl fluoride again, sealing the reaction kettle and reacting at 60 ℃ for 10 hours, reducing the pressure of the reaction kettle from 0.26MPa to 0.1MPa, recovering the excessive trifluoromethanesulfonyl fluoride, distilling and removing 38L of solvent to obtain yellow viscous solid, adding 40 kg of ethanol, quickly stirring, filtering to obtain white crystals, drying to obtain 32.8 kg of refined product, wherein the purity is 99.5%, and the yield is 92.1%.
Example 3
9.3 kg of aniline, 45L of acetonitrile and 15 kg of triethylene diamine are added into a 100L stainless steel reaction kettle, and a trifluoromethanesulfonyl fluoride steel cylinder is connected. The reaction kettle is pumped to-0.09 Mpa, 30 kg of trifluoromethanesulfonyl fluoride gas is introduced, and the reaction kettle is sealed. The reaction is stirred for 8 hours under the condition of room temperature, the pressure of the reaction kettle is gradually reduced from 0.25MPa to 0.1MPa, and no obvious change is caused within half an hour. And opening the acyl fluoride recovery pipeline, recovering the excessive acyl fluoride, and closing the acyl fluoride recovery pipeline after the pressure of the reaction kettle is reduced to 0 Mpa. The distillation system was opened and 40L of acetonitrile was distilled off. Then adding 45L of dichloromethane and 0.4 kg of 4-dimethylaminopyridine, introducing 23 kg of trifluoromethanesulfonyl fluoride again, sealing the reaction kettle for 16 hours, reducing the pressure of the reaction kettle from 0.22MPa to 0.06MPa, recovering the excessive trifluoromethanesulfonyl fluoride, distilling to remove 40L of solvent to obtain yellow viscous solid, adding 45 kg of ethanol, quickly stirring, filtering to obtain white crystals, and drying to obtain 32.6 kg of fine product with the purity of 99.1% and the yield of 91.5%.
The embodiments of the present invention have been described in detail, but the description is only for the preferred embodiments of the present invention and should not be construed as limiting the scope of the present invention. All changes, modifications and equivalents that may be made without departing from the spirit and scope of the invention are intended to be covered by the appended claims.
Claims (10)
1. A preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide is characterized by comprising the following steps: the method comprises the steps of taking trifluoromethanesulfonyl fluoride as a raw material, reacting organic base serving as an acid-binding agent with aniline in a strong polar solvent to generate N-phenyl trifluoromethanesulfonyl amide, and reacting the N-phenyl trifluoromethanesulfonyl amide with trifluoromethanesulfonyl fluoride in a weak polar solvent to obtain N-phenyl bis (trifluoromethanesulfonyl) imide.
2. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 1, characterized in that: the method comprises the following specific steps:
adding organic base serving as an acid-binding agent into a polar solvent, adding aniline, and introducing excessive trifluoromethanesulfonyl fluoride to prepare N-phenyltrifluoromethanesulfonamide;
distilling to remove the polar solvent, adding the weak polar solvent and the catalyst, and introducing excessive trifluoromethanesulfonyl fluoride to obtain a crude product of the N-phenyl bis (trifluoromethanesulfonyl) imide;
distilling to remove the weak polar solvent, and washing with an alcohol solvent to obtain a refined N-phenyl bis (trifluoromethanesulfonimide);
preferably, the molar ratio of trifluoromethanesulfonyl fluoride to aniline is 1.1-5: 1;
preferably, the molar ratio of organic base to aniline is 2-4: 1;
preferably, the molar ratio of catalyst to aniline is 0.005-0.2: 1.
3. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 2, characterized in that: in the second step and the third step, the excess trifluoromethanesulfonyl fluoride is recovered before the polar solvent or the weakly polar solvent is recovered.
4. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 1 or 2, characterized in that: the organic base is one of triethylene diamine, hexamethylene tetramine and 1, 8-diazabicycloundecen-7-ene (DBU).
5. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 1 or 2, characterized in that: the catalyst is 4-dimethylamino pyridine or 4-pyrrolyl pyridine.
6. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 1 or 2, characterized in that: the polar solvent is one or a mixture of more of acetonitrile, N-dimethylformamide, N-dimethylacetamide, nitromethane, chlorobenzene, 1, 2-dichloroethane, chloroform, carbon tetrachloride, acetone, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether and ethylene glycol diethyl ether;
preferably, the polar solvent is acetonitrile, N-dimethylformamide or N, N-dimethylacetamide.
7. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 1 or 2, characterized in that: the weak polar solvent is one or a mixture of more of dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, toluene, benzene and tetrahydrofuran.
8. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 1 or 2, characterized in that: the alcohol solvent is one or more of methanol, ethanol and isopropanol.
9. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 2, characterized in that: the reaction temperature of the first step is 0-80 ℃, and the reaction temperature of the second step is-20-80 ℃;
preferably, the reaction temperature of the first step is 40-80 ℃, and the reaction temperature of the second step is 20-80 ℃.
10. The process for the preparation of N-phenyl bis (trifluoromethanesulfonyl) imide according to claim 2, characterized in that: the mass ratio of the alcohol solvent to the crude product of the N-phenyl bis (trifluoromethyl) sulfimide is 0.5-5: 1.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112375016A (en) * | 2020-11-17 | 2021-02-19 | 江西国化实业有限公司 | Preparation process of N-phenyl bis (trifluoromethanesulfonimide) |
| CN112710757A (en) * | 2020-12-23 | 2021-04-27 | 九江天赐高新材料有限公司 | Method for detecting N-phenyl bis (trifluoromethanesulfonimide) |
| CN112830887A (en) * | 2020-12-30 | 2021-05-25 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113801040A (en) * | 2021-10-11 | 2021-12-17 | 石家庄圣泰化工有限公司 | Synthesis method of N, N-dimethyl trifluoromethanesulfonamide |
| CN113880733A (en) * | 2021-10-29 | 2022-01-04 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112375016A (en) * | 2020-11-17 | 2021-02-19 | 江西国化实业有限公司 | Preparation process of N-phenyl bis (trifluoromethanesulfonimide) |
| CN112710757A (en) * | 2020-12-23 | 2021-04-27 | 九江天赐高新材料有限公司 | Method for detecting N-phenyl bis (trifluoromethanesulfonimide) |
| CN112710757B (en) * | 2020-12-23 | 2022-05-17 | 九江天赐高新材料有限公司 | Method for detecting N-phenyl bis (trifluoromethanesulfonimide) |
| CN112830887A (en) * | 2020-12-30 | 2021-05-25 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113801040A (en) * | 2021-10-11 | 2021-12-17 | 石家庄圣泰化工有限公司 | Synthesis method of N, N-dimethyl trifluoromethanesulfonamide |
| CN113880733A (en) * | 2021-10-29 | 2022-01-04 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113880733B (en) * | 2021-10-29 | 2022-04-05 | 中船(邯郸)派瑞特种气体股份有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
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Application publication date: 20200612 |