13140-51-7

Upstream product

• 64-17-5 ethanol 
• 103-71-9 phenyl isocyanate 
• 108-44-1 1-amino-3-methylbenzene 
• 18824-43-6 N-carbamimidoyl-N'-phenyl-urea 
• 591-17-3 meta-bromotoluene 
• 64-10-8 phenyl carbamate 
• 17933-03-8 m-tolylboronic acid 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 62-53-3 aniline 
• 313549-89-2 (1H-benzo-[d][1,2,3]triazol-1-yl)(m-tolyl)methanone 
• 500-72-1 oxanilic acid 
• 67-66-3 chloroform 
• 625-95-6 3-Iodotoluene 
• 621-30-7 3-methylphenyl isothiocyanate 

Relevant academic research and scientific papers

Nitroarenes as versatile building blocks for the synthesis of unsymmetrical urea derivatives and N-Arylmethyl-2-substituted benzimidazoles

In this contribution, a fast and simple method for the synthesis of unsymmetrical urea derivatives and N-arylmethyl-2-substituted benzimidazoles was developed starting from nitroarenes. The reaction of nitroarenes and phenyl isocyanate or phenyl isothiocyanate in tin (II) chloride dihydrate/choline chloride eutectic mixture afforded the expected urea and thiourea derivatives, while the reaction of different aldehydes with o-nitroaniline or 4-methoxy-2-nitroaniline shows a markedly high preference for the obtention of N-arylmethyl-2-substituted benzimidazoles over the 2-substituted analogues. This method offers a straightforward alternative to obtain the target compounds in good to excellent yields with short reaction times employing an operationally simple experimental set-up. Graphic abstract: [Figure not available: see fulltext.] A series of unsymmetrical urea and thiourea derivatives together with 1,2-disubstituted benzimidazoles are easily obtained in good yields starting from nitroarenes employing the eutectic mixture tin (II) chloride dihydrate/choline chloride as reductive reaction media.

Photocatalyzed synthesis of unsymmetrical ureas via the oxidative decarboxylation of oxamic acids with PANI-g-C3N4-TiO2 composite under visible light

The synthesis of unsymmetrical ureas via the photocatalyzed oxidative decarboxylation of oxamic acids has been developed. The carbamoyl radicals were generated from oxamic acids in the presence of a hypervalent iodine reagent and the PANI(Polyaniline)-g-C3N4-TiO2 composite under visible light irradiation. The radicals were converted in situ into the corresponding isocyanates, which were then trapped by amines to afford the corresponding products in moderate to good yields. This protocol avoided the direct use of environmentally unfriendly isocyanates and a series of substrates were tolerated. Moreover, the photocatalyst could be readily recovered by simple filtration and be reused for several runs with only a slight decrease in the catalytic activity.

An Improved Synthesis of Urea Derivatives from N -Acylbenzotriazole via Curtius Rearrangement

The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N -acyl, and cyclic ureas in good yields from N -acylbenzotriazoles by treating the latter with various amines in the presence of TMSN 3 /Et 3 N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.

Synthetic method and application of urea compound

The invention relates to a synthetic method of a urea compound, comprising the following steps: adding substituted oxazolone and sodium acetate into a methanol solution, and adding substituted amine under the stirring condition, reacting and carrying out column chromatography to obtain the urea compound. The defect that dangerous compounds need to be used during existing synthetic process is overcome, and a one-pot method is adopted to replace an existing reaction with low yield. The method of the invention has mild reaction condition, the operation is simple, raw materials are easily available, and the substrate can be converted into various other useful molecules. The compound has strong practicality, and can be applied to synthesis of the pesticide daimuron, dieresis long and the anti-cancer drug Sorafenib. The invention relates to a green and environmentally-friendly unsymmetrical urea compound synthesis method with simple process and low cost.

Pd/C-Catalyzed Domino Synthesis of Urea Derivatives Using Chloroform as the Carbon Monoxide Source in Water

A Pd/C-catalyzed domino synthesis of symmetrical and unsymmetrical ureas from aryl iodides, sodium azide, amines and CHCl3 in water has been developed. This reaction proceeds with sequential carbonylation, Curtius rearrangement and nucleophilic addition. CHCl3 serves as a convenient and safe alternation of CO gas in the presence of KOH. A series of urea derivatives were obtained in moderate to good yields with good functional group tolerance. Furthermore, the Pd/C catalyst could be readily recovered with slight decrease in the catalytic activity after six consecutive runs. (Figure presented.).

Synthesis of unsymmetrical ureas and S-thiocarbamates under catalyst-free conditions in a [BMIM]BF4 ionic liquid

Unsymmetrical ureas and Sthiocarbamates were prepared in good to excellent yields by direct condensation of phenylurea with amines and thiols in 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) without the addition of any additives. The [BMIM]BF4 ionic liquid is a mild medium and can be recycled and reused several times.

Cu(acac)2-catalyzed N-arylations of phenylurea with aryl boronic acid

Cu(acac)2 activates aryl boronic acids for the reaction with NH2-phenylurea without additional ligand and heating. The procedure is simple, general, ligand-free, milder than the palladium-catalyzed arylation, and avoids the use of toxic phosphine ligands. Copyright Taylor & Francis Group, LLC.

Microwave assisted, solvent- and ligand-free copper catalyzed N-arylation of phenylurea with aryl halides

An inexpensive and efficient catalyst system has been developed for the N-arylation of phenylurea including a variety of aryl halides. This simple protocol uses Cu2O as the catalyst, microwave assisted, solvent- and ligand-free, K3PO4.H2O as the base.

An efficient and mild protocol for the synthesis of unsymmetrical ureas in the absence of catalyst and additives

A new practical method for the synthesis of unsymmetrical ureas was achieved by reaction of phenylurea with primary and secondary amines under neutral and mild condition in very good yields. The reaction took place in refluxing dioxane and does not require any catalyst or additives.

Variation of xanthene-based bidentate ligands in the palladium-catalyzed arylation of ureas

A series of xanthene-based bidentate ligands containing various substituents on diphenylphosphino groups were synthesized and tested in the palladium-catalyzed arylation reaction of urea with unactivated aryl bromides. It was found that both steric and electronic properties of the ligands have a pronounced effect on the yields and ratios of the products. Arylation of urea and phenylurea with unactivated aryl bromides in the presence of Pd2dba3·CHCl3/3,5-(CF3) 2Xantphos and Cs2CO3 as base in dioxane at 100°C gave the corresponding N,N′-diarylureas in 62-98% yields.