111382-87-7

Upstream product

• 95-68-1 2,4-Xylidine 
• 1042161-72-7 C₁₅H₁₄N₄ 
• 1187386-92-0 N-(3,5-dimethylphenyl)benzimidamide 
• 100-47-0 benzonitrile 
• 108-69-0 3,5-dimethylaminoaniline 
• 100-46-9 benzylamine 
• 98-80-6 phenylboronic acid 
• 98-88-4 benzoyl chloride 
• 6328-77-4 N-(2,4-dimethylphenyl)benzamide 
• 139765-24-5 benzoic acid-(2,4-dimethyl-6-nitro-anilide) 
• 110513-22-9 N-(2,4-dimethyl-phenyl)-benzamide oxime 
• 698-16-8 benzohydroximoyl chloride 
• 108837-61-2 N-(2,4-dimethylphenyl)benzimidamide 

Relevant academic research and scientific papers

Transforming Oxadiazolines through Nitrene Intermediates by Energy Transfer Catalysis: Access to Sulfoximines and Benzimidazoles

Subtle differences in reaction conditions facilitated unprecedented photocatalytic reactions of oxadiazolines by energy transfer catalysis. A set of compounds, sulfoximines and benzimidazoles, were ingeniously prepared from oxadiazolines via nitrene intermediates by photocatalytic N-O/C-N bond cleavages. The synthesis of sulfoximines was realized through intermolecular N-S bond formation between nitrene intermediates and sulfoxides, whereas benzimidazoles were obtained via intramolecular aromatic substitution of the nitrene to the tethered aryl substituent.

New synthesis method of thiabendazole

The invention relates to a new synthetic route of a drug commonly named as thiabendazole. Thiazole-4-formaldehyde is used as a raw material, and is condensed with hydroxylamine hydrochloride to obtainthiazole-4-formaldoxime, thiazole-4-formaldoxime is subjected to chlorination by using NCS, and then reacts with aniline to obtain N-phenylthiazole-4-methylamine oxime, then N-phenylthiazole-4-methylamine oxime reacts with p-trifluoromethyl benzoyl chloride to obtain an amidoxime ester, and finally a visible-light-catalyzed free radical reaction is adopted for cyclization to obtain thiazole. According to the method, the visible-light-catalyzed free radical reaction is used to the synthesis of thiabendazole for the first time, the reaction conditions of a high temperature and a strong acid inthe traditional synthesis method are avoided, and thereby the reaction is greener and milder. The method has a broad spectrum, and can also be used for synthesis of imidazole compounds Ia-Ial.

Formation of Amidinyl Radicals via Visible-Light-Promoted Reduction of N-Phenyl Amidoxime Esters and Application to the Synthesis of 2-Substituted Benzimidazoles

We have developed a new method for the synthesis of 2-substituted benzimidazoles via amidinyl radicals generated by visible-light-promoted reduction of N-phenyl amidoxime esters in the presence of an iridium photocatalyst. This is the first report of the use of N-phenyl amidoxime esters as amidinyl radical precursors, and the first use of substituted benzene rings as amidinyl radical acceptors. This method widens the application range of substrates and overcomes the shortcomings of the traditional methods for the synthesis of 2-substituted benzimidazoles, which requires harsh reaction conditions, involves difficult-to-prepare substituted o-phenylenediamine substrates, and produces acidic waste.

Method for catalytically synthesizing benzimidazole compound in water phase under microwave radiation

The invention discloses a method for catalytically synthesizing a benzimidazole compound in a water phase under microwave radiation. The method comprises the following steps: adding a catalytic amount of metal chloride, proline lithium and a substituted 2-halogenated aniline substrate, ammonia water, a benzaldehyde derivative, inorganic alkali and water into a reaction container; putting the reaction container into a microwave reaction instrument to react at certain temperature and under certain power; after certain time, decompressing and concentrating; purifying a product through a column chromatography to obtain the benzimidazole compound, wherein the metal chloride in the step is iron chloride, cobalt chloride, nickel chloride or copper chloride, the inorganic alkali in the step is sodium hydroxide, cesium carbonate, sodium carbonate, potassium hydroxide or potassium phosphate, and reaction temperature of the microwave reaction instrument is 20 DEG C to 200 DEG C. The method for preparing the benzimidazole compound, provided by the invention, is environmental-friendly, is simple and convenient to operate, is safe and cheap and is efficient. Compared with the prior art, the method has the advantages of moderate reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.

Denitrogenative Imidoyl Radical Cyclization: Synthesis of 2-Substituted Benzoimidazoles from 1-Azido-2-isocyanoarenes

A novel access to 2-substituted benzoimidazoles, through unprecedented denitrogenative imidoyl radical cyclization of 1-azido-2-isocyanoarenes, has been developed. This tandem radical process was initiated by adding a C- or P-centered radical to isocyanide, followed by cycloaddition of the imidoyl radical to the azido group. Then, nitrogen loss and hydrogen abstraction of the resulting aminyl radical from surroundings delivered 2-substituted benzoimidazoles. Carbon radicals generated from another annulation process could also be applied, furnishing various heterocycle linked benzoimidazole derivatives.

Copper(II)-Catalyzed Oxidative Cross-Coupling of Anilines, Primary Alkyl Amines, and Sodium Azide Using TBHP: A Route to 2-Substituted Benzimidazoles

Copper(II)-catalyzed oxidative cross-coupling of anilines, primary alkyl amines, and sodium azide is described in the presence of TBHP at moderate temperature. This one-pot multicomponent protocol involves a domino C-H functionalization, transimination, ortho-selective amination, and a cyclization sequence. The broad substrate scope and functional group compatibility are the significant practical features. The protocol can be extended to the coupling of benzyl alcohols with moderate yields.

Synthesis of benzimidazoles by PIDA-promoted direct C(sp2)-H imidation of N-arylamidines

A metal-free synthesis of diversified benzimidazoles from N-arylamidines through a phenyliodine(III) diacetate (PIDA) promoted intramolecular direct C(sp2)-H imidation has been developed. The reaction proceeds smoothly at 0 °C or ambient temperature to provide the desired products in good to excellent yields. The synthesis of 2-alkyl- or 2-alkyl-fused benzimidazoles, which are generally inaccessible by similar Pd- or Cu-catalyzed approaches, can also be achieved. Copyright

N-chlorosuccinimide/sodium hydroxide-mediated synthesis of benzimidazoles from amidines under mild conditions

A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.

Direct imidation to construct 1H-benzo[d]imidazole through Pd II-catalyzed C-H activation promoted by thiourea

A study was conducted to demonstrate the development of a method to construct 1H-benzo[d]immidazole through PdII -catalyzed intermolecular C-H activation starting from N-phenylbenziimidamide. The detailed mechanism investigations indicated that a palladacycle monomer or dimer was the key intermediate for this transformation, demonstrating that thiourea was first used to influence the efficiency of C-H activation. The method was found to construct 1H-benzo[d]immidazole through PdII -catalyzed intermolecular C-H activation extending the substrate scope widely. It also demonstrated the introduction of thiourea (tetramethylthiourea) (TMTU) for the first time as an additive to promote the efficiency of PdII catalysis for the direct C-H transformation. N-phenylbenziimidamide was also readily synthesized through the addition of aniline to benzonitrile according to the method to conduct the investigations.

Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides

(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.