57883-78-0

Upstream product

• 3173-53-3 Cyclohexyl isocyanate 
• 109-89-7 diethylamine 
• 92109-08-5 cyclohexylcarbamic acid 4-nitrophenyl ester 
• 96-49-1 [1,3]-dioxolan-2-one 
• 108-91-8 cyclohexylamine 
• 931-53-3 Cyclohexyl isocyanide 

Downstream Products

• 766-93-8 N-cyclohexylformamide 

Relevant academic research and scientific papers

Chemoselective isocyanide insertion into the N-H bond using iodine-DMSO: Metal-free access to substituted ureas

Insertion of isocyanides into the N-H bond gives access to many medicinally important and structurally diverse complex nitrogen-containing heterocycles. Although the transition metal catalyzed isocyanide insertion into the N-H bond is very common, polymerization of isocyanides in the presence of a transition metal and their strong coordination with metals are the common drawbacks. On the other hand, the inertness of most of the isocyanides towards amines in the absence of a metal catalyst has stymied the growth of the metal-free approach for isocyanide insertion into amines. As a result, only a handful of metal catalysed methods with limited substrate scopes have been reported for the synthesis of ureas via isocyanide insertion into amines and no metal-free version has been reported yet. Interestingly, chemoselective isocyanide insertion into amines has not been reported in the literature. We employed the I2-DMSO reagent system for the chemoselective synthesis of ureas, where isocyanides react with aliphatic amines only, while aromatic amines need a nucleophilic activator (DABCO) to facilitate the formation of ureas. This method gave direct and chemoselective access to ureas by evading the commonly used yet toxic isocyanates.

Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent

Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable to the presence of catalyst and solvent. The preliminary investigation of the reaction mechanism showed that alkyl ammonium alkyl carbamate was quickly formed as the intermediate, and then the final product was formed by the intramolecular dehydration.

Organocatalyzed synthesis of ureas from amines and ethylene carbonate

A new solventless method for the synthesis of symmetrical and unsymmetrical ureas, starting from ethylene carbonate and amines, is reported. 1,5,7-Triazabicyclo[4.4.0]dec-5-ene(TBD) and thioureas have been found to be efficient organocatalysts for this reaction.

A New Convenient Method for the Synthesis of Symmetrical and Unsymmetrical N,N'-Disubstituted Ureas

A new method is described for the preparation of symmetrically and unsymmetrically disubstituted ureas by aminolysis of bis(4-nitrophenyl) carbonate.The second substitution is slower than the first one, and it is possible to isolate monosubstituted intermediates when equimolar amounts of substrates are used.The reaction of the intermediates with different amines give unsymmetrical derivatives of urea.