51-36-5Relevant articles and documents
Reactions of bisdiazonium salts derived from monosubstituted m-phenylenediamines with amides and nitriles of unsaturated acids under anionarylation conditions
Baranovskii,Yatsyuk,Vasilenko,Grishchuk
, p. 1821 - 1825 (2015)
Reactions of 5-carboxy and 4-methylphenylene-1,3-bisdiazonium tetrafluoroborates with amides and nitriles of acrylic and methacrylic acids in the presence of chloride, bromide, and thiocyanate anions proceed as anionarylation at one of the diazo groups and nucleophilic substitution at another one. With 4-methylphenylene- 1,3-bisdiazonium tetrafluoroborate as the arylating agent, the anionarylation and the Sandmeyer reaction occur involving para- and ortho-positioned diazo groups, respectively.
Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides
O'Brien, Connor J.,Nicewicz, David A.
supporting information, p. 814 - 816 (2021/03/01)
The use of carbon dioxide as a C1 chemical feedstock remains an active field of research. Here we showcase the use of milled dry ice as a method to promote the availability of CO 2in a reaction solution, permitting practical synthesis of arylcarboxylic acids. Notably, the use of milled dry ice produces marked increases in yields relative to those obtained with gaseous CO 2, as previously reported in the literature.
Synthesis of Dichlorobenzamide Derivatives: Crystal Structures of 3,5-Dichloro-N-(2-chlorophenyl)benzamide and 3,5-Dichloro-N-(4-chlorophenyl)benzamide
Zhang, Jun,Li, Yue,Wang, Bei,Jia, Ai-Quan,Zhang, Qian-Feng
, p. 108 - 115 (2020/02/18)
Abstract: Reactions of 3,5-dichlorobenzoyl chloride and arylamine compounds in N,N′-dimethylformamidesolution at 60 °C afforded a series of dichlorobenzamidederivatives 4–14 in good yields. These new compounds and accompanyingintermediates were characterized and confirmed by nuclear magneticresonance and infrared spectroscopy, of which structures of compounds 4and 6 were established by X-ray crystallography. Compound 4 crystallizesin triclinic space group Pī, with a = 5.047 (18), b = 10.28 (4), c = 13.36 (5) ?, α =107.59 (5)°, β = 93.55 (5)°, γ = 98.34 (5)°, and Z = 2. The unit cell of 6 has a monoclinic Pn symmetry with the cell parameters a = 9.581 (3), b = 12.217 (4), c = 11.072 (3) ?, β = 92.584 (4)°, and Z = 4. Graphic Abstract: A series of 3,5-dichlorobenzamide compounds were synthesized from reactions of arylamine compounds with 3,5-dichlorobenzoyl chloride, which was prepared from 3,5-dichlorobenzonitrile.[Figure not available: see fulltext.]
Synthesis method of 2-amino-5-chloro-N,3-dimethylbenzamide
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, (2017/07/19)
The invention discloses a synthesis method of 2-amino-5-chloro-N,3-dimethylbenzamide, belonging to the technical field of organic chemical synthesis. The method comprises the following steps: carrying out oxidation under the catalytic actions of N-hydroxyphthalimide and cobalt acetylacetonate to generate benzoic acid, carrying out substitution reaction with chlorine gas to generate 3,5-dichlorobenzoic acid, shielding off 5- chlorine by using a shielding reagent, carrying out methyl substitution on the 5- chlorine by using a Grignard reagent to generate 3-methyl-5-chlorobenzoic acid, carrying out nitro-substitution on the 3-methyl-5-chlorobenzoic acid and nitric acid under the catalytic action of concentrated sulfuric acid to generate 2-nitro-3-methyl-5-chlorobenzoic acid, carrying out catalytic hydrogenation to reduce the nitro group into amino group, carrying out reaction under the actions of N,N'-diisopropylcarbodiimide and 1-hydroxybenztriazole to obtain an intermediate, and carrying out reaction on the intermediate and methylamine to obtain the 2-amino-5-chloro-N,3-dimethylbenzamide. The method is simple to operate, and obviously enhances the synthesis yield to 92% or above.
