- A PROCESS FOR THE SYNTHESIS ANTHRANILIC DIAMIDE COMPOUNDS AND INTERMEDIATES THEREOF
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The present invention disclosed a process for the synthesis of anthranilic diamide compound of formula (I), wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6 and Z are as defined in the detailed description. The process comprising the step of obtaining a mono- or dicyano substituted aniline compound of formula (IV) which is then converted to an anthranilic acid compound of formula (V) or an anthranilic amide compound of formula (Va). Further, the compound of formula (VI) can be optionally synthesized from compound of formula (IV or V or Va).
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Page/Page column 22
(2020/09/08)
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- METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0149-0152
(2020/07/28)
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- Method of catalytically synthesizing polybromo-aniline in water phase
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The invention discloses a method of catalytically synthesizing polybromo-aniline in a water phase. The method comprises following steps: adding a catalytic amount of a free radical initiator, aniline derivatives, cheap and low-toxic bromine salts, and water into a reactor; carrying out reactions in a photocatalytic reaction instrument under power of 5W at a room temperature; after a while, extracting the reaction product by ethyl acetate, and carrying out recrystallization to obtain polybromo-aniline; wherein the free radical initiator is eosin, sodium persulfate, or potassium persulfate. The power of the incandescent lamp of the photocatalytic reaction instrument is 5W. The free radical initiator and bromine salts are cheap and easily available. The method is an ideal synthesis method of polybromo-aniline. Cheap and low-toxic bromine salts are used to replace liquid bromine. The cheap and easily available free radical initiator is used to replace unstable and explosive hydrogen peroxide. After 4 to 10 hours of reactions under the power of 5W, polybromo-aniline can be synthesized, the yield and the reaction selectivity are high, the byproducts are few, and the post treatment is simple.
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Paragraph 0012; 0018
(2019/10/04)
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- Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach
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A simple, environmentally benign methodology has been developed to synthesize some bromoorganic compounds which have potential as antimicrobial agents. The required compounds were obtained through microwave (MW) irradiation, on-water reactions and using cetyltrimethylammonium tribromide (CTMATB) as the bromine source. The high yield of the product could be achieved within short reaction times, thus representing the main attribute of the present synthetic approach. The compounds were evaluated for in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Bacillus subtilis. Further, in silico studies were carried out to elucidate the interactions of the compounds with the bacterial proteins.
- Longkumer, Naruti,Richa, Kikoleho,Karmaker, Rituparna,Kuotsu, Visekhonuo,Supong, Aola,Jamir, Latonglila,Bharali, Pranjal,Sinha, Upasana Bora
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p. 276 - 283
(2019/07/12)
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- New insights into bromination process: Effective preparation of Ambroxol
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Ambroxol used as an expectorant in treating respiratory diseases was effectively prepared with a total yield of 62 %, with o-toluidine as the feedstock via successive procedures of electrophilic bromination, acetylation, radical benzylic bromination, N-alkylation and hydrolysis processes. The addition of aqueous hydrogen peroxide could enhance the utilisation of liquid bromine in the electrophilic bromination of o-toluidine, avoiding the hazardous HBr generated as a by-product. In addition, liquid bromine promoted by MnO2 was used efficiently for the radical benzylic bromination of N-acetyl-N-(2,4-dibromo-6-methylphenyl)acetamide under mild conditions.
- Xu, Jun-Hui,Ma, Yan-Qiong,Wei, Jian-Ping,Li, Fang-Mei,Peng, Xin-Hua
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p. 722 - 728
(2015/04/14)
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- Preparation of carbazole and dibenzofuran derivatives by selective bromination on aromatic rings or benzylic groups with N-bromosuccinimide
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N-Bromosuccinimide (NBS), a bromine source, has been used to study the bromination of toluidine and cresols systematically to clarify the underlying mechanism and the orientation effect. It has been found that bromination of toluidine and cresols which possess electron-donating NH2/OH with NBS gives electrophilic aromatic substitution products quickly instead of the desired benzylic bromination products. In contrast, when the electronic effect of the substituted groups is reversed, only the benzylic bromination products are gained. Based on this methodology, several potential AChE inhibitors, such as 2-methoxy-5-(benzylamino)methyl-dibenzofuran, 3-bromo-2-methoxy-5-methyl-9H- carbazole, 3,6-dibromo-2-methoxy-5-methyl-9H-carbazole, and 5-(bromomethyl)-2- methoxy-9H-(phenylsulfonyl)-carbazole have been synthesized.
- Fang, Lei,Zhang, Haun,Fang, Xubin,Gou, Shaohua,Cheng, Lin
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p. 635 - 641
(2014/06/23)
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- Selective bromination of pyrrole derivatives, carbazole and aromatic amines with DMSO/HBr under mild conditions
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Bromination of pyrrole derivatives, carbazole and aromatic amines using the DMSO/HBr system affords high yields of the corresponding bromo compounds. Temperature control used in the bromination of anilines helped to promote selective formation of mono- or di-brominated products. Simple operation, low toxicity and high selectivity make this a promising new procedure for the bromination of aromatic compounds.
- Liu, Cong,Dai, Rongji,Yao, Guowei,Deng, Yulin
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p. 593 - 596
(2015/01/09)
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- Effect of structural factors and solvent nature in bromination of anilines
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Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.
- Bagmanov
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experimental part
p. 1570 - 1576
(2011/06/20)
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- A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions
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Regioselective oxidative bromination of electron-rich aromatic rings has been studied using potassium bromide as a bromine source in the presence of benzyltriphenylphosphonium peroxymonosulfate as oxidant under nearly neutral reaction conditions. In most cases we obtained monobrominated derivatives regioselectively and in good to high yields without the aid of strong acids.
- Adibi, Hadi,Hajipour, Abdol R.,Hashemi, Majid
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p. 1255 - 1259
(2007/10/03)
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- 1-Benzyl-4-aza-1-azoniabicyclo[2.2.2] octane tribromide as a highly reactive brominating agent for aniline derivatives
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Reaction of anilines with 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide (3) in the presence of CaCO3 in small amounts of methanol gave brominated aromatic amines in good yields at room temperature. The isolation of products is straightforward.
- Hajipour,Imanieh,Pourmousavi
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p. 4597 - 4604
(2007/10/03)
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- Novel bromination method for anilines and anisoles using NH 4Br/H2O2 in CH3COOH
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A simple, efficient, regioselective, environmentally safe, and economical method for the oxybromination of anilines and anisoles without catalyst is reported. The electrophilic substitution of bromine generated in situ from ammonium bromide as a bromine source and hydrogen peroxide as an oxidant for the first time.
- Krishna Mohan,Narender,Srinivasu,Kulkarni,Raghavan
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p. 2143 - 2152
(2007/10/03)
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- Pyridinium dichlorobromate: A new stable brominating agent for aromatic compounds
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Pyridinium dichlorobromate (PyHBrCl2, 1) is a new example of iminium-trihalide complexes. The compound is prepared from pyridine and chlorine in the presence of aqueous hydrogen bromide. The crystalline trihalide is quite stable and acts as a safe source of positive bromine. It shows a remarkable reactivity towards aromatic compounds compared with other bromine complexes. It is also considered as a potential source for bromine chloride BrCl.
- Muathen, Hussni A.
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p. 169 - 171
(2007/10/03)
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- Solid state nuclear bromination with N-bromosuccinimide. Part 1. Experimental and theoretical studies on some substituted aniline, phenol and nitro aromatic compounds
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Solid state bromination of a number of substituted phenol, aniline and nitro aromatic compounds with N-bromosuccinimide yields exclusively the nuclear brominated products. Reactivity in the solid state depends on the reaction time, temperature and nature of the substituent on the substrate. The reaction apparently proceeds by an electrophilic aromatic substitution pathway. Molecular orbital and reaction free energy calculations also support such a view. Thermal analysis and video microscopic observation reveal the nature of the solid state reaction. Crystallinity is required for the reactivity and product selectivity. Product yield decreases with loss of selectivity when the reaction is carried out in a melt or in solution. Unlike the topochemical solid state reactions wherein molecular packing is more important than the intrinsic reactivity, these reactions demonstrate the importance of both these factors.
- Sarma, Jagarlapudi A.R.P.,Nagaraju, Akula
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p. 1113 - 1118
(2007/10/03)
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- Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines
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A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.
- Pews,Hunter,Wehrmeyer
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p. 4809 - 4820
(2007/10/02)
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- BROMINATION OF ANILINES BY BENZYLTRIPHENYLPHOSPHONIUM TRIBROMIDE
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Anilines and benzyltriphenylphosphonium tribromide in dichloromethane and methanol medium in the presence of sodium bicarbonate react within a few minutes at room temperature to give the corresponding polybromoanilines in good yields.
- Xin-teng, Ding,Guo-bin, Liu
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p. 1261 - 1266
(2007/10/02)
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- Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide
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The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane-methanol containing calcium carbonate powder for 0.5 h at room temperature gave bromo-substituted aromatic amines in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Inoue, Kazuhisa,Kondo, Manabu,Nakamura, Hiroko,et al.
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p. 597 - 599
(2007/10/02)
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