99-30-9Relevant articles and documents
Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/01/04)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
Synthesis method of 2, 6-dichloro-4-aminophenol
-
Paragraph 0023; 0031-0032; 0035-0036; 0039-0040, (2021/06/12)
The invention discloses a synthesis method of 2, 6-dichloro-4-aminophenol, and belongs to the field of preparation of pesticide, medicine and dye intermediates, 2, 6-dichloro-4-aminophenol is obtained by adopting paranitroaniline as a raw material through the steps of chlorination, diazonium hydrolysis, hydrogenation and the like, methanol is adopted as a solvent for chlorination, filtrate can be repeatedly used, and the use of a large amount of acid water is reduced; toluene is selected as a solvent in diazotization, diazonium liquid is directly layered after being hydrolyzed, an organic layer is separated out, water vapor distillation is not needed, and the distillation risk and energy consumption are reduced; toluene is selected as a hydrogenation solvent, and an organic layer separated after the diazonium liquid is hydrolyzed is directly hydrogenated, so that the process flow is simplified.
Identification of Potent and Selective Inhibitors of Fat Mass Obesity-Associated Protein Using a Fragment-Merging Approach
Elboray, Elghareeb E.,Fujiwara, Yoshie,Itoh, Yukihiro,Kitao, Yuki,Kotoku, Masayuki,Mellini, Paolo,Oba, Makoto,Obika, Satoshi,Prakash, Muthuraj,Roy, Rohini,Singh, Ritesh,Suzuki, Takayoshi,Takada, Yuri,Takahashi, Yukari,Terao, Mitsuhiro,Wang, Dan Ohtan,Yamaguchi, Takao,Yamamoto, Chika,Yamashita, Yasunobu
supporting information, p. 15810 - 15824 (2021/11/18)
Fat mass obesity-associated protein (FTO) is a DNA/RNA demethylase involved in the epigenetic regulation of various genes and is considered a therapeutic target for obesity, cancer, and neurological disorders. Here, we aimed to design novel FTO-selective inhibitors by merging fragments of previously reported FTO inhibitors. Among the synthesized analogues, compound 11b, which merges key fragments of Hz (3) and MA (4), inhibited FTO selectively over alkylation repair homologue 5 (ALKBH5), another DNA/RNA demethylase. Treatment of acute monocytic leukemia NOMO-1 cells with a prodrug of 11b decreased the viability of acute monocytic leukemia cells, increased the level of the FTO substrate N6-methyladenosine in mRNA, and induced upregulation of MYC and downregulation of RARA, which are FTO target genes. Thus, Hz (3)/MA (4) hybrid analogues represent an entry into a new class of FTO-selective inhibitors.
Environment-friendly 2, 6-dichloro-4-nitroaniline preparation method
-
, (2020/08/27)
The invention discloses an environment-friendly 2, 6-dichloro-4-nitroaniline preparation method, and belongs to the field of environmental protection. The environment-friendly 2, 6-dichloro-4-nitroaniline preparation method comprises the following steps: step 1, adding o-dichlorobenzene, namely a component shown as a formula (I), into a nitric acid and sulfuric acid solution for reaction to obtainm-nitro-1, 2-dichlorobenzene, namely a component shown as a formula (II); step 2, adding the m-nitro-1, 2-dichlorobenzene obtained in the step 1 into an ammonia water solution for reaction to obtain2-chloro-4-nitroaniline, namely a component shown as a formula (III); step 3, dropwise adding hydrochloric acid and a hydrogen peroxide solution into the 2-chloro-4-nitroaniline obtained in the step 2. According to the new preparation method, the generation of polychlorophenol during the 2, 6-dichloro-4-nitroaniline preparation process is effectively reduced, the environmental protection meets therequirements of OECO-Textile 100, and a dye obtained after the actual production of the preparation method directly meets the requirements of OECO-Textile 100.
Identification of novel scaffold using ligand and structure based approach targeting shikimate kinase
Rahul Reddy,Krishnasamy, Sivakumar Kullampalayam,Kathiravan
, (2020/08/05)
Tuberculosis (TB) remains a major global health problem. It causes ill-health among millions of people each year and rank as the second leading cause of death from an infectious disease worldwide, after the human immunodeficiency virus (HIV). Shikimate kinase is one of the major enzymes targeted for TB. Most approaches to overcome TB were based on synthesis and screening of a known compounds to obtain a few representatives with desired potency. In this study, we have applied a virtual screening approach which combines ligand- and structure-based approaches to screen a large library of compounds as a starting point for the identification of new scaffolds for the development of shikimate kinase inhibitors. The combined approach has identified 2 new scaffolds as potential inhibitors of shikimate kinase. To prove the approach, few of the molecules and their derivatives, a total of 17 compounds, were synthesized. The compounds were tested for biological activity and shows moderate activity against shikimate kinase. The shikimate kinase enzyme inhibition study reveals that the compounds showed inhibition (IC50) at concentrations of 50 μg/mL (Compounds 21, 22, 24, 25, 26, 27, 30, 32, 34) and 25 μg/mL (14, 19, 23, 31, 33).
General and selective synthesis of primary amines using Ni-based homogeneous catalysts
Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Jiao, Haijun,Murugesan, Kathiravan,Wei, Zhihong
, p. 4332 - 4339 (2020/05/18)
The development of base metal catalysts for industrially relevant amination and hydrogenation reactions by applying abundant and atom economical reagents continues to be important for the cost-effective and sustainable synthesis of amines which represent highly essential chemicals. In particular, the synthesis of primary amines is of central importance because these compounds serve as key precursors and central intermediates to produce value-added fine and bulk chemicals as well as pharmaceuticals, agrochemicals and materials. Here we report a Ni-triphos complex as the first Ni-based homogeneous catalyst for both reductive amination of carbonyl compounds with ammonia and hydrogenation of nitroarenes to prepare all kinds of primary amines. Remarkably, this Ni-complex enabled the synthesis of functionalized and structurally diverse benzylic, heterocyclic and aliphatic linear and branched primary amines as well as aromatic primary amines starting from inexpensive and easily accessible carbonyl compounds (aldehydes and ketones) and nitroarenes using ammonia and molecular hydrogen. This Ni-catalyzed reductive amination methodology has been applied for the amination of more complex pharmaceuticals and steroid derivatives. Detailed DFT computations have been performed for the Ni-triphos based reductive amination reaction, and they revealed that the overall reaction has an inner-sphere mechanism with H2metathesis as the rate-determining step.
Cyclic synthesis method of nitroaniline chloride
-
Paragraph 0032; 0033; 0038; 0039, (2020/10/05)
The invention discloses a cyclic synthesis method of nitroaniline chloride. The cyclic synthesis method comprises the following steps: (1) mixing nitroaniline and sulfuric acid, and preheating to a chlorination reaction temperature; (2) respectively inputting the solution obtained in the step (1) and chlorine into a reactor to carry out a chlorination reaction, cooling the material obtained in thereaction to obtain a supersaturated solution, and crystallizing to separate out a supersaturated product namely nitroaniline chloride; and (3) carrying out solid-liquid separation on the material cooled in the step (2), carrying out flash evaporation on the obtained saturated nitroaniline chloride/sulfuric acid solution, recycling hydrogen chloride, and circulating hydrogen chloride to the step (1) to replace sulfuric acid for dissolving nitroaniline, thereby realizing cyclic synthesis of nitroaniline chloride. Product super-saturation precipitation and saturated solution circulation are realized, the proportion of raw materials in a reaction system is reduced, the reaction is promoted to enter a uniform liquid phase system, meanwhile, mother liquor can be recycled, and the purposes of high efficiency, controllability and comprehensive utilization of resources are achieved.
2,6-dichloro-4-nitroaniline low-temperature synthesis method
-
Paragraph 0038; 0039; 0091, (2017/04/04)
The invention discloses a low-temperature synthesis method of 2,6-dichloro-4-nitroaniline. The method comprises the following steps sequentially: (1) by taking 20-35% diluted hydrochloric acid or a filtrate obtained in the following step (2) as a solvent I, firstly adding p-nitroaniline into the solvent I, then, introducing chlorine gas for chlorination reaction, naturally standing a reaction solution at room temperature after the reaction ends, and filtrating so as to obtain 2,6-dichloro-4-nitroaniline and hydrochloric acid mother liquor; (2) by taking the hydrochloric acid mother liquor as a solvent II, adding the solvent II into a three-mouthed flask, then, adding p-nitroaniline, dropwise adding hydrogen peroxide, carrying out stirring reaction while carrying out heat preservation after dropwise adding is completed, naturally standing at room temperature after the reaction ends so as to precipitate solid, and filtrating, thereby obtaining 2,6-dichloro-4-nitroaniline and the filtrate. 2,6-dichloro-4-nitroaniline synthesized by adopting the method disclosed by the invention has advantages of low cost, high atomic economical efficiency, no wastewater discharge, environment friendliness, high efficiency and the like.
A chlorine direct chlorination and at the same time the hydrogen peroxide oxidizing chloride preparation of 2,6-dichloro-4-nitroaniline method
-
Paragraph 0037-0039, (2017/02/02)
The invention relates to a method for preparing 2,6-dichloro-4-nitroaniline through direct chlorination of chlorine gas and oxidative chlorination of hydrogen peroxide. The method comprises the following steps: (1) adding paranitroaniline into hydrochloric acid at the concentration of 5-35wt%, heating to 40-80 DEG C, stirring for uniformly mixing, slowly inflating the chlorine gas within 0.5-5h, slowly adding hydrogen peroxide dropwise, and after adding the chlorine gas and the hydrogen peroxide, continuing to preserve heat and react for 0.3-1.5h; (2) filtering a product obtained in the step (1), washing a filter cake to be neutral, and drying to obtain the 2,6-dichloro-4-nitroaniline. By regulating a dosage ratio of the chlorine gas to the hydrogen peroxide, the concentration of the hydrochloric acid in a reaction system can be kept unchanged, the reaction process is steady and easily controlled, and the product is high in yield and purity.
Clean technology for continuously synthesizing 2,6-dichloro-p-nitroaniline
-
Paragraph 0042; 0043; 0044; 0045; 0046, (2016/12/16)
A clean technology for continuously synthesizing 2,6-dichloro-p-nitroaniline adopts multistage serially connected reaction kettles and comprises the following steps: continuously adding 2,4-dinitroaniline, hydrochloric acid and chlorine to a first stage reaction kettle, carrying out a chlorination reaction under stirring, allowing parts of a material in a previous reaction kettle to enter a self reaction kettle through a pump and to circulate, allowing parts of the material in the previous reaction kettle to enter a next reaction kettle, continuously carrying out the chlorination reaction, allowing tail gas generated in the previous reaction kettle to enter the next reaction kettle, continuously carrying out the chlorination reaction, allowing parts of a material in a final stage reaction kettle to enter the self reaction kettle through a pump and to circulate, continuously discharging and filtering parts of the final obtained material after a detection result shows the reaction is completed to obtain a filter cake which is a 2,6-dichloro-p-nitroaniline product, allowing a mother liquor obtained after filtration to enter a mother liquor recovery tank, blowing air to the mother liquor in the mother liquor recovery tank, reusing hydrogen chloride tail gas obtained after blowing, pumping the blown mother liquor with certain acidity into a mother liquor storage tank, and recycling the mother liquor in the mother liquor storage tank to substitute hydrochloric acid.
