6531-31-3

Usage

Synthesis Reference(s)

Synthesis, p. 1032, 1983 DOI: 10.1055/s-1983-30616

InChI:InChI=1/C4H8N2O/c1-3-2-5-4(7)6-3/h3H,2H2,1H3,(H2,5,6,7)

Upstream product

• 82831-19-4 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester 
• 23589-75-5 5-(2,4-dichloro-phenyl)-[1,3,4]oxathiazol-2-one 
• 78-90-0 1,2-diaminopropan 
• 67337-69-3 methyl-5 hydantoine 
• 201230-82-2 carbon monoxide 
• 57-13-6 urea 
• 124-38-9 carbon dioxide 
• 1192-34-3 4-methyl-1,3-dihydro-imidazol-2-one 

Downstream Products

• 19777-66-3 (racemi)-1,2-diaminopropane dihydrochloride 

Relevant academic research and scientific papers

SBA-15 Supported Dendritic ILs as a Green Catalysts for Synthesis of 2-Imidazolidinone from Ethylenediamine and Carbon Dioxide

In this work, a simple and facile approach is conducted for preparing many new SBA-15 supported dendritic imidazolium ILs heterogeneous catalysts SBA-15/IL(1–3) having high ionic density from SBA-15. SBA-15/IL(3) as a green heterogeneous catalyst can be used for synthesis of 2-imidazolidinone from ethylenediamine and carbon dioxide and considering solvent-free condition. SBA-15/IL(3) showed to have the highest catalytic activity besides a positive dendritic influence on the yields of the synthesis of 2-imidazolidinone in the presence of CO2 is seen because of existing the high-density peripheral zwitterionic ionic liquid functional groups on the biobased SBA-15/IL(3) catalyst surfaces. Graphical Abstract: [Figure not available: see fulltext.]

METHOD OF PREPARING UREA USING AMINE COMPOUND AND CARBON DIOXIDE

Disclosed is a production method of urea using an amine compound and carbon dioxide. The production method of urea includes a step of producing urea by using the amine compound and a 2-pyrrolidone derivative as a solvent and reacting with the carbon dioxide, thereby producing high yield cyclic urea under mild reaction conditions and no catalyst conditions.

Rhodium(III)-catalyzed Intermolecular Unactivated Secondary C(sp3)?H Bond Amidation Directed by 3,5-dimethylpyrazole

A Rh(III)-catalyzed intermolecular unactivated secondary C(sp3)?H bond amidation via nitrene insertion directed by 3,5-dimethylpyrazole is reported. This procedure tolerates a broad substrate scope including chain and cyclic N-alklyamides. Notably, the directing group 3,5-dimethylpyrazole of chain N-alkylamide substrates could be easily removed via cascade intermolecular amidation and intramolecular cyclization in one-pot affording the sulfonylureas by increasing the reaction temperature. (Figure presented.).

Efficient Non-Catalytic Carboxylation of Diamines to Cyclic Ureas Using 2-Pyrrolidone as a Solvent and a Promoter

Carboxylation reactions of diamines were found to proceed rapidly and non-catalytically, producing corresponding cyclic ureas in excellent yields and selectivities when 2-pyrrolidone (2-PY) was used as a solvent. A similar promoting effect with 2-PY was also observed for the carboxylation of monoamines by carbon dioxide (CO2). Most notably, the carboxylation reactions of mono- and diamines conducted in 2-PY afforded 2–4 times higher yields of corresponding dialkyl ureas and cyclic ureas compared with those in N-methyl-2-pyrrolidone (NMP). Such a dramatic promoting effect using 2-PY is believed to be associated with the multiple hydrogen bonding interactions between 2-PY and the CO2-containing species of amines. Due to such favorable interactions, carboxylation reactions seem to be more facilitated in 2-PY than in NMP. (Figure presented.).

Ionic liquids/ZnO nanoparticles as recyclable catalyst for polycarbonate depolymerization

A useful protocol for waste bis-phenol A-polycarbonates (BPA-PC) chemical recycling is proposed based on a bifunctional acid/basic catalyst composed by nanostructured zinc oxide and tetrabutylammonium chloride (ZnO-NPs/NBu4Cl) in quality of Lewis acid and base, respectively. Retro-polymerization reaction proved to be of general application for several nucleophiles, including water, alcohols, amines, polyols, aminols and polyamines, leading to the complete recovery of BPA monomer and enabling the PC polymer to function as a green carbonylating agent (green phosgene alternative) for preparing carbonates, urethanes and ureas. A complete depolymerization can be obtained in seven hours at 100 °C and ZnO nanocatalyst can be recycled several times without sensible loss of activity. Remarkably, when polycarbonate is reacted with glycerol, it is possible to realize in a single process the conversion of two industrial wastes (BPA-PC and glycerol) into two valuable chemicals like BPA monomer and glycerol carbonate (the latter being a useful industrial solvent and fuel additive).

N-VINYLIMIDAZOLIDONE COMPOUND, AND POLYMER THEREOF

PROBLEM TO BE SOLVED: To provide an N-vinylimidazolidone compound polymer that is expected to be applied for a cell culture material, a temperature-responsive material and others. SOLUTION: The present invention provides a polymer polymerized with an N-vinylimidazolidone compound (1) as a monomer, or a copolymer comprising the monomer and a monomer of a different structure (R1 is H, C1-12 alkyl or acyl; R2 and R3 is H or methyl). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Highly efficient synthesis of cyclic ureas from CO2 and diamines by a pure CeO2 catalyst using a 2-propanol solvent

Pure cerium oxide (CeO2) acts as an effective and reusable heterogeneous catalyst for direct synthesis of cyclic ureas from CO2 and diamines even at a low CO2 pressure of 0.3 MPa. 2-Propanol is the most preferable solvent to provide good selectivity. The system composed of a CeO2 catalyst and a 2-propanol solvent is applied to various diamines to provide the corresponding cyclic ureas in high yields (78-98%), including six-membered-ring ureas that are difficult to be synthesized from CO 2. Based on the kinetic studies on the effect of CO2 pressure and amine concentration and FTIR studies on adsorption of ethylenediamine and CO2 onto CeO2, the following mechanism for the synthesis of cyclic urea is proposed: (1) formation of carbamic acid and carbamate species on CeO2, (2) decomposition of carbamic acid to a free amino group and CO2, (3) nucleophilic attack of the amino group on the carbamate on CeO2 to produce the cyclic urea and (4) desorption of the product and regeneration of CeO2.

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.

Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations

Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such as SOCl2, TsCl, or AcCl. The intramolecular trapping of the activated carbamate by a hydroxyl group leads to the formation of 2-oxazolidinones or 2-oxazinones in good to excellent yields. This methodology was successfully applied to the synthesis of cyclic ureas up to 7-membered rings from the corresponding diamines.

Synthesis of urea derivatives from CO2 and amines catalyzed by polyethylene glycol supported potassium hydroxide without dehydrating agents

Polyethylene glycol supported potassium hydroxide (KOH/PEG1000) was developed as a recyclable catalyst for facile synthesis of urea derivatives from amines and CO2 without utilization of additional dehydrating agents. Primary aliphatic amines, secondary aliphatic amines, and diamines can be converted into the corresponding urea derivatives in moderate yields. Furthermore, the catalyst can be recovered after a simple separation procedure, and reused over 5 times with retention of high activity. Georg Thieme Verlag Stuttgart.