5198-48-1

Basic information

• Product Name: 2-Oxazolidinone, 3-(4-methoxyphenyl)-
• CAS NO: 5198-48-1
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Mol File: 5198-48-1.mol

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3-(4-methoxyphenyl)-(5198-48-1)
• EPA Substance Registry System: 2-Oxazolidinone, 3-(4-methoxyphenyl)-(5198-48-1)

Safety Data

• Hazardous Substances Data: 5198-48-1(Hazardous Substances Data)

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 104-94-9 4-methoxy-aniline 
• 497-25-6 dimethylenecyclourethane 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 75-21-8 oxirane 
• 124-38-9 carbon dioxide 
• 5602-93-7 ethyl (2-hydroxyethyl)carbamate 
• 2933-77-9 N-(2-hydroxyethyl)-4-methoxyaniline 
• 105-58-8 Diethyl carbonate 
• 7451-55-0 ethyl 4-methoxyphenylcarbamate 
• 106-93-4 ethylene dibromide 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 28690-23-5 3-(4-methoxyphenyl)thiazolidin-2-one 
• 2933-77-9 N-(2-hydroxyethyl)-4-methoxyaniline 
• 1313524-89-8 C₁₆H₁₃F₂NO₃ 
• 33141-33-2 3-(4-methoxyphenylamino)propanenitrile 

Relevant articles and documents

Synergetic activation of CO2by the DBU-organocatalyst and amine substrates towards stable carbamate salts for synthesis of oxazolidinones

The development of an efficient methodology to transform CO2 into valuable chemicals has attracted increasing attention concerning the challenging issues of CO2-utilization. Herein, an efficient approach for the preparation of oxazolidinones from CO2, primary (aliphatic/aromatic) amines and 1,2-dichloroethane (or its derivatives) catalyzed by DBU organo-superbase was achieved with yields of 47-97% under mild conditions (80-100 °C, 12 h, 1.0 MPa CO2). Control experiments demonstrated that the formation of an ion-pair carbamate salt intermediate IS-B derived from the reaction of CO2, DBU (catalyst) and an amine (substrate) was the key step for this three-component reaction. The available DBU-amine-CO2 adduct intermediate (like IS-B-2) with fair stability will evolve into the thermodynamically stable product oxazolidinones upon attack of 1,2-dichloroethane (or its derivatives), along with the regeneration of the DBU catalyst. Alternatively, the decomposition of the DBU-aryl amine-CO2 adduct (like IS-B-1) with relatively poor stability also could result in the competitive substitution reaction of 1,2-dichloroethane (or its derivatives) with the aryl amine. This work provides insights into synergetic CO2-activation by the DBU-catalyst and a nucleophilic amine-substrate via the formation of robust carbamate salt intermediates responsible for the final production of oxazolidinones. This journal is

The Synthesis of 3-Aryl-2-oxazolidinones from CO2, Ethylene Oxide, and Anilines Under Mild Conditions Using PVA-DFNT/Ni

Abstract: A novel nanocatalyst design using nanomaterials through active-zone crystallisation was proposed. The hydrothermal crystallisation of amorphous dendritic fibrous nano-titanium dioxide with Ni (DFNT/Ni) sites was determined to be the main step in producing extremely active dendritic DFNT/Ni zones, which in turn dramatically enhanced their catalytic activities. DFNT/Ni was then combined with polyvinyl alcohol (PVA) by using a traditional individual-nozzle electrospinning method, and the resulting material was named PVA-DFNT/Ni. This method was utilised to produce 3-aryl-2-oxazolidinones from ethylene oxide, CO2, and anilines. The prepared catalytic apparatus was eco-friendly and had the advantages of high catalytic activity, ability to improve the reaction mixture, and reusability without a considerable decrease in efficiency. It is extracted in the straight and adoptive chemical fixation of flue-gas CO2 obtained from industrial emissions, thereby achieving high degrees of CO2 absorption and conversion. Graphic Abstract: [Figure not available: see fulltext.].

Method for synthesizing cyclic amide from carbon dioxide

The invention discloses a method for synthesizing cyclic amide from carbon dioxide. An aromatic amino compound, 1 atm carbon dioxide and a halogenated compound undergo a one-step reaction under the synergistic action of N-doped TiO2 and an inorganic salt catalyst to generate the cyclic amide. Studies find that visible light has an obvious promoting effect on the conversion process. The chemical selectivity of the cyclic amide compound can be regulated by regulating conditions such as reaction temperature, time and illumination. The catalyst can be recycled for five times after being separatedand dried, and the activity and the chemical selectivity can be well maintained. The synthesis method has the advantages of simple synthetic route, novelty, simple process, high yield and high purityof the product, cheap and easily available catalyst, no influences on the environment, and suitableness for industrial production.

Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide

An effective three-component fixation of atmospheric CO2 with readily available 1,2-dichloroethane and aromatic amine toward oxazolidinones catalyzed by in situ NHC was developed. The reaction occurred in good to excellent yields with good gene

Spirulina (Arthrospira) platensis Supported Ionic Liquid as a Catalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Epoxide, Anilines

Abstract: This study investigates the potential application of the (Ammonio)butane-1-sulfonate modified Spirulina (Arthrospira) platensis biomasses in the synthesis of 3-aryl-2-oxazolidinones from CO2, ethylene oxide, and anilines. High catalytic activity and ease of recovery from the reaction mixture using filtration and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system. The effects of the structure of ionic liquid on the catalytic performance were investigated and the various reaction conditions were optimized. This observation was exploited in the direct and selective chemical fixation of CO2, affording high degrees of CO2 capture and conversion. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis of N-aryl-2-oxazolidinones from cyclic carbonates and aromatic amines catalyzed by bio-catalyst

A convenient and effective method of synthesizing 3-aryl-2-oxazolidinones from cyclic carbonates and aryl amines catalyzed by bio-catalyst adenine in the presence of Et3N under solvent-free conditions is described. The protocol is suitable for the wide scope of substrates, e.g. cyclic carbonates with or without substitutes, and aryl amines with either electron-withdrawing or electron-donating group. The products were obtained in good to excellent yields under the optimal conditions, even in steric hindered cases. The effect of reaction time, temperature, loading of catalyst, and amount of starting materials in the reaction were investigated, and the reaction mechanism is discussed.

Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides

Cu2O/N,N′-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramolecular cross-coupling product.

A straightforward one-pot synthesis of bioactive: N -aryl oxazolidin-2-ones via a highly efficient Fe3O4@SiO2-supported acetate-based butylimidazolium ionic liquid nanocatalyst under metal- and solvent-free conditions

In the present study, we report the fabrication and characterization of novel acetate-based butylimidazolium ionic liquid immobilized silica-coated magnetic nanoparticles (IL-OAc@FSMNP). The synthesized nanocomposite proves its supremacy as an environmentally benign catalyst in the reaction of aniline and its derivatives with ethylene carbonate to form bioactive N-aryl oxazolidin-2-ones under metal-, ligand-, and solvent-free conditions. The catalyst offers excellent assemblies of hydrogen-bond donors and acceptors, which activate the substrates, thereby delivering good-to-excellent product yields with a conversion and selectivity of more than 99%. Additionally, mild reaction conditions, wide substrate scope, effortless catalytic recovery and recyclability of the catalyst up to eight consecutive cycles offer the potential for scale-up in various pharmaceutical applications.

A One-Pot Synthesis of N-Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes

The multicomponent assembly of pharmaceutically relevant N-aryl-oxazolidinones through the direct insertion of carbon dioxide into readily available anilines and dibromoalkanes is described. The addition of catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional-group tolerance under ambient CO2pressure and mild temperature. This report also provides the first proof-of-principle for the single-operation synthesis of elusive seven-membered ring cyclic urethanes.

Selective Synthesis of 5-Substituted N-Aryloxazolidinones by Cycloaddition Reaction of Epoxides with Arylcarbamates Catalyzed by the Ionic Liquid BmimOAc

A selective procedure for the synthesis of 5-substituted N-aryloxazolidinones by the coupling of epoxides with arylcarbamates catalyzed by ionic liquids has been developed. The effects of reaction time, reactant molar ratio, amount of catalyst, and temper