31502-57-5

Usage

InChI:InChI=1/C9H16ClNO2/c10-6-7-13-9(12)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,12)

Upstream product

• 13027-13-9 2-hydroxyethyl N-cyclohexylcarbamate 
• 124-38-9 carbon dioxide 
• 108-91-8 cyclohexylamine 
• 107-06-2 1,2-dichloro-ethane 
• 90957-40-7 N^ε-(2-Chloroethoxycarbonyl)-N^ε-nitroso-L-lysine 
• 627-11-2 2-Chloroethyl chloroformate 

Downstream Products

• 6162-80-7 N-Nitro-N-cyclohexyl-carbamidsaeure-<2-chlor-aethylester> 
• 55390-61-9 3-cyclohexyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Cooperative Catalysis of Ru(III)-Porphyrin in CO2-Involved Synthesis of Oxazolidinones

CO2-transformations into high value-added products have become a fascinating area in green chemistry. Herein, a Ru(III)-porphyrin catalyst (RuCl3 ? 3H2O?H2TPP) was found highly efficient in the three-component reaction of CO2, aliphatic amines and dichloroethane (or its derivative) for synthesis of oxazolidinones in the yields of 71～91%. It was indicated by means of the control experiments and UV-vis spectra that CO2 was stoichiometrically activated by the involved aliphatic amine substrates to form a stable carbamate salt while 1,2-dichloroethane (or its derivative) was independently activated by the involved Ru(III)-porphyrin catalyst. The combination of CO2-activation by aliphatic amines with 1,2-dichloroethane activation by Ru(III)-porphyrin catalyst cooperatively contributed to this successful transformation.

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