1852-17-1

Usage

Synthesis Reference(s)

Synthetic Communications, 36, p. 835, 2006 DOI: 10.1080/00397910500464228

Upstream product

• 1120-81-6 pyrrolidin-2-one oxime 
• 109-76-2 Trimethylenediamine 
• 616-38-6 carbonic acid dimethyl ester 
• 105-58-8 Diethyl carbonate 
• 20112-81-6 2-(methylthio)-1,4,5,6-tetrahydropyrimidine 
• 872-34-4 2-imino-pyrrolidine 
• 201230-82-2 carbon monoxide 
• 67-52-7 BARBITURIC ACID 
• 444-15-5 5-hydroxybarbituric acid 
• 557-01-7 Pyrimidin-2(1H)-one 
• 109-94-4 formic acid ethyl ester 
• 67-56-1 methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 

Downstream Products

• 82822-14-8 1-Morpholinomethyl-tetrahydro-2(1H)-pyrimidinone 
• 82822-17-1 1,3-Bis-(morpholinomethyl)-tetrahydro-2(1H)-pyrimidinone 
• 4673-45-4 1,3-Dibutyl-hexahydropyrimid-2-on 
• 102233-94-3 N,N'-1,3-bisphenylmethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone 
• 30826-85-8 1,3-Diaethyl-tetrahydro-1H-pyrimidin-2-on 
• 7226-23-5 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone 
• 34790-81-3 1-(3-nitro-benzyl)-tetrahydro-pyrimidin-2-one 
• 815-06-5 N-methyl-2,2,2-trifluoroacetamide 
• 18132-77-9 1,3-bis(trimethylsilyl)tetrahydropyrimidin-2-one 
• 30826-87-0 N,N'-dipropyl-N,N'-propyleneurea 
• 62641-66-1 N-nitrosotetrahydro-2(1H)-pyrimidone 
• 23947-52-6 1-(2-methoxy-phenyl)-tetrahydro-pyrimidin-2-one 
• 946123-68-8 1,3-bis(4-formylphenyl)tetrahydropyrimidin-2(1H)-one 
• 65347-82-2 6-Nitrobenzoyleneurea 

Relevant academic research and scientific papers

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.

Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene

The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.

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.).

Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation

A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.

Ruthenium-Catalyzed Urea Synthesis by N-H Activation of Amines

Activation of the N-H bond of amines by a ruthenium pincer complex operating via amine-amide metal-ligand cooperation is demonstrated. Catalytic formyl C-H activation of N,N-dimethylformamide (DMF) is observed in situ, which resulted in the formation of CO and dimethylamine. The scope of this new mode of bond activation is extended to the synthesis of urea derivatives from amines using DMF as a carbon monoxide (CO) surrogate. This catalytic protocol allows the synthesis of simple and functionalized urea derivatives with liberation of hydrogen, devoid of any stoichiometric activating reagents, and avoids the direct use of fatal CO. The catalytic carbonylation occurred at low temperature to provide the formamide; a formamide intermediate was isolated. The consecutive addition of different amines provided unsymmetrical urea compounds. The reactions are proposed to proceed via N-H activation of amines followed by CO insertion from DMF and with liberation of dihydrogen.

Efficient Reversible Hydrogen Carrier System Based on Amine Reforming of Methanol

A novel hydrogen storage system based on the hydrogen release from catalytic dehydrogenative coupling of methanol and 1,2-diamine is demonstrated. The products of this reaction, N-formamide and N,N′-diformamide, are hydrogenated back to the free amine and methanol by a simple hydrogen pressure swing. Thus, an efficient one-pot hydrogen carrier system has been developed. The H2 generating step can be termed as "amine reforming of methanol" in analogy to the traditional steam reforming. It acts as a clean source of hydrogen without concurrent production of CO2 (unlike steam reforming) or CO (by complete methanol dehydrogenation). Therefore, a carbon neutral cycle is essentially achieved where no carbon capture is necessary as the carbon is trapped in the form of formamide (or urea in the case of primary amine). In theory, a hydrogen storage capacity as high as 6.6 wt % is achievable. Dehydrogenative coupling and the subsequent amide hydrogenation proceed with good yields (90% and >95% respectively, with methanol and N,N′-dimethylethylenediamine as dehydrogenative coupling partners).

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).

Ruthenium-Catalyzed Urea Synthesis Using Methanol as the C1 Source

An unprecedented protocol for urea synthesis directly from methanol and amine was accomplished. The reaction is highly atom-economical, producing hydrogen as the sole byproduct. Commercially available ruthenium pincer complexes were used as catalysts. In addition, no additive, such as a base, oxidant, or hydrogen acceptor, was required. Furthermore, unsymmetrical urea derivatives were successfully obtained via a one-pot, two-step reaction.

Hydrogen bond organocatalysis of benzotriazole in transamidation of carboxamides with amines

A new method of transamidation of carboxamides with amines catalyzed by benzotriazole has been developed.

Process for the Synthesis of Cyclic Alkylene Ureas

The invention relates to a process for the synthesis of cyclic alkylene ureas comprising reacting a difunctional amine A having two primary amino groups, and an aliphatic organic carbonate component C selected from the group consisting of dialkyl carbonates CD and of alkylene carbonates CA, wherein the ratio of the amount of substance n(-NH2) of primary amino groups -NH2 in the difunctional amine A to the sum n(C) of the amount of substance n(CD) of carbonate groups of a dialkyl carbonate CD and the amount of substance n(CA) of carbonate groups in an alkylene carbonate CA, is at least more than 2, and to the product obtained by this process.