- Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imine
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The invention relates to a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imine, and belongs to the technical field of chemical engineering. The method comprises the following steps: dissolving trifluoromethanesulfonic acid and organic alkali in an organic solvent, and adding HATU for reaction; the reaction temperature is greater than or equal to 15 DEG C, and the organic solvent is not boiled; after the reaction is finished, a reaction solution containing trifluoromethanesulfonic acid active ester is obtained; adding aniline into the reaction liquid, and reacting at 25 +/-5 DEG C for 6-12 hours; and after the reaction is finished, removing the organic solvent to obtain a crude product containing the N-phenyl bis (trifluoromethanesulfonyl) imine, washing, and recrystallizing and purifying by using an alcohol solvent with 1-3 carbon atoms to obtain the N-phenyl bis (trifluoromethanesulfonyl) imine. The N-phenyl bis (trifluoromethanesulfonyl) imine with high purity and high yield can be prepared by the method, the reaction condition is mild, the utilization rate of raw materials is high, and the method is green and environment-friendly.
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Paragraph 0026-0052
(2022/01/12)
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- Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction
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An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.
- Chaturvedi, Jagriti,Haldar, Chabush,Bisht, Ranjana,Pandey, Gajanan,Chattopadhyay, Buddhadeb
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supporting information
p. 7604 - 7611
(2021/05/26)
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- Preparation method of N-phenyl-bis(trifluoromethanesulfonyl)imide
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The invention provides a preparation method of N-phenyl-bis(trifluoromethanesulfonyl)imide. The preparation method comprises the following steps: subjecting trifluoromethanesulfonic acid to reacting with thionyl chloride to produce trifluoromethanesulfonyl chloride; and dissolving aniline in a solvent, adding organic alkali such as triethylamine as an acid-binding agent, and dropwise adding trifluoromethanesulfonyl chloride to prepare N-phenyl-bis(trifluoromethanesulfonyl)imide. According to the invention, raw materials are cheap and easily available; trifluoromethanesulfonyl chloride participates in reaction, the utilization rate of groups is high, and the reaction is efficient; special devices such as low-temperature or under-pressure devices are not needed, and operation is easy; and basically no solid three wastes are generated.
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Paragraph 0026; 0028; 0029; 0031; 0032; 0034-0035
(2021/05/26)
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- Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide
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The invention discloses a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide. According to the method, trifluoromethanesulfonyl fluoride is adopted as a raw material, in a strong polar solvent, organic alkali is adopted as an acid-binding agent to react with aniline to generate N-phenyl trifluoromethanesulfonamide, most of the solvent is removed through distillation, a weak polarsolvent and a catalyst are added, trifluoromethanesulfonyl fluoride continues to be introduced for the reaction, and N-phenyl bis (trifluoromethanesulfonyl) imide is prepared. According to the scheme,the cost is low, the reaction is mild, excessive trifluoromethanesulfonyl fluoride cannot be discharged to generate pollution without using shielding gas, the prepared product is high in purity and yield, and industrial popularization can be achieved.
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Paragraph 0047-0050
(2020/07/02)
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- Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imide
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The invention relates to a method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imide, and belongs to the technical field of preparation of perfluoroalkyl sulfonylation reagents. According to the method, perfluoroalkyl sulfonyl fluoride and aniline are used as raw materials, and N-phenyl-bis (perfluoroalkyl sulfonyl) imide is prepared under the action of a catalyst. The method disclosed bythe invention is simple in process flow, mild in reaction, good in safety, low in cost, high in yield and high in purity.
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Paragraph 0025-0030
(2020/01/12)
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- DIRECT OXIDATIVE AMINATION OF HYDROCARBONS
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Provided is a process for converting a hydrocarbon comprising at least one C-H bond to a nitrogen-functionalized product. The process comprises contacting a hydrocarbon and (i) an oxidizing electrophile comprising (a) a main group element or transition metal in oxidized form and (b) at least one nitrogen-containing ligand, or (ii) an oxidant and a reduced form of an oxidizing electrophile comprising (a) a main group element or transition metal and (b) at least one nitrogen-containing ligand, in a solvent to provide the nitrogen-functionalized product and an electrophile reduction product. Further provided is an oxidizing composition comprising the oxidizing electrophile with at least one nitrogen-containing ligand and a non?oxidizable liquid.
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Paragraph 0156; 0191-0193
(2019/06/17)
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- PIPERIDINE UREAS AS CATHEPSIN CYSTEINE PROTEASE INHIBITORS
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The present invention relates to substituted piperidine urea derivatives that are inhibitors of cathepsin K proteases and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of these enzymes. In addition, the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of bone diseases such as osteoporosis and osteoarthritis as well as other diseases and conditions. The compounds have the general formula: [Formula should be inserted here]
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Page/Page column 69-70
(2016/03/14)
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- METALLO-BETA-LACTAMASE INHIBITORS
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The present invention relates to compounds of formula (I) that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.
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Paragraph 0357
(2016/12/01)
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- Synthesis method of trimethoxystilbene
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The invention discloses a synthesis method of trimethoxystilbene. The method comprises the following steps of (1) at room temperature, adding trifluoromethanesulfonic acid into dichloromethane; stirring the mixture; slowly dripping sulfoxide chloride; after the dripping is completed, performing stirring reaction for 12 hours at room temperature; concentrating a reaction system to obtain a coarse product of trifluoromethanesulfonyl chloride; (2) adding aniline and triethylamine into dichloromethane; lowering the temperature to 0 DEG C; dripping the obtained coarse product of trifluoromethanesulfonyl chloride through a dropping funnel; after the dripping is completed, raising the temperature to room temperature for reaction for 2 hours; performing water washing, drying and concentration on the reaction system; then, performing recrystallization by petroleum ether to obtain trimethoxystilbene. The synthesis method has the beneficial effects that the raw materials of trifluoromethanesulfonic acid used by the synthesis method of trimethoxystilbene provided by the invention are common chemical raw materials; the price is low; the acquisition is easy; the cost is greatly reduced; special equipment such as low-temperature kettles is not needed in the production process; the operation is easy; the method is suitable for industrial production.
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Paragraph 0014
(2016/10/09)
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- COMPOSITIONS AND METHODS FOR MODULATING DNA METHYLATION
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Disclosed herein are compositions and methods for modulating DNA methylation of one or more gene promoters, treating a subject diagnosed with or suspected of having a disease or disorder characterized by DNA hypermethylation, decreasing c-myc expression, increasing desmoplakin expression, and inhibiting metastases. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
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Paragraph 0163; 0171
(2015/02/25)
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- METALLO-BETA-LACTAMASE INHIBITORS
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The present invention relates to compounds of formula (I) that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.
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Page/Page column 58
(2015/08/06)
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- COMPOUNDS AND COMPOSITIONS FOR STABILIZING HYPOXIA INDUCIBLE FACTOR-2 ALPHA AS A METHOD FOR TREATING CANCER
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Disclosed herein is {[5-(3-fluorophenyl)-3-hydroxypyridine-2-carbonyl]-amino}acetic acid and the ester and amide prodrugs thereof, that can stabilize hypoxia inducible factor-2 alpha (HIF-2α) and thereby provide a method for treating cancer. Further disclosed are compositions which comprise {[5-(3-fluorophenyl)-3-hydroxypyridine-2-carbonyl]-amino}acetic acid and/or a prodrug thereof which can be used to treat cancer.
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Page/Page column 7-8
(2013/02/27)
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- 1-(2-PHENOXYMETHYLHETEROARYL)PIPERIDINE AND PIPERAZINE COMPOUNDS
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The invention relates to compounds of formula I: where X, HAr, a, and R1 through R6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. The compounds of formula I are serotonin and norepinephrine reuptake inhibitors. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.
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Page/Page column 17
(2011/10/10)
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- N-(trifluoromethylsulfonyl)aryloxytrifluoromethylsulfoximines [ArO-SO(CF3)=NTf] and N-aryltriflimides Ar-N(Tf)2 by thermal and photolytic dediazoniation of [ArN2][BF4] in [BMIM][Tf2N] ionic liquid: Exploiting the ambident nucleophilic character of a "nonnucleophilic" anion
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(Chemical Equation Presented) Arenediazonium tetrafluoroborate salts undergo metathesis on immobilization in 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonato)amide [BMIM][Tf2N]. The "noncoordinating", "nonnucleophilic" [Tf2N] anion acts as an ambident nucleophile toward the aryl cations, formed via thermal dediazoniation, to give predominantly the oxy anion quenching products [ArO-SO(CF3)=NTf], with minimal formation of ArN(Tf)2, irrespective of the nature of the substituent(s) on the ArN2 +. Strong preference for the formation of oxygen trapping products did not change under photolytic conditions, where dediazoniation occurs at room temperature. A minimal amount of the Schiemann product ArF is also formed in both thermal and photolytic dediazoniation, depending on the substituent(s). Progress of dediazoniation in the IL (both thermal and photolytic) and the evolution of the products were directly monitored by 1H and 19F NMR. According to DFT (Density Functional Theory) calculations, PhN(Tf)2 is more stable than PhO-SO(CF3)=NTf by 15-17 kcal/mol, depending on the basis set. Inclusion of solvation effects (PCM, with acetone and with CH2ClCH2Cl as solvent) did not change this preference. The [ArN2][BF4] dediazoniation in [BMIM][Tf2N] resulted in synthesis and characterization of a series of hitherto unknown [ArO-SO(CF3)=NTf] compounds. The X-ray structure of MesO-SO(CF3)=NTf (Mes = mesityl) is reported. On the basis of extraction studies, suitable solvent systems have been identified that remove the products without dissolving [BMIM][NTf2], thus overcoming product recovery difficulties typically associated with the use of this IL.
- Laali, Kenneth K.,Okazaki, Takao,Bunge, Scott D.
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p. 6758 - 6762
(2008/02/10)
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- The "non-nucleophilic" anion [Tf2N]- competes with the nucleophilic Br-: An unexpected trapping in the dediazoniation reaction in ionic liquids
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Imidazolium ionic liquids containing [Tf2N]- anion are not as innocent as they are often considered; [Tf2N]- is more reactive than Br- in heterolytic dediazoniation reactions. The Royal Society of Chemistry 2006.
- Bini, Riccardo,Chiappe, Cinzia,Marmugi, Elisa,Pieraccini, Daniela
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p. 897 - 899
(2008/02/08)
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