Method for preparing symmetric urea compound

Abstract

The invention provides a novel reaction system for synthesizing a symmetric urea compound by taking CO2 as a carbonylation reagent, wherein Lewis base and hydrosilane are used as accelerators and efficiently enable an aromatic / aliphatic primary amine compound to react with normal-pressure CO2 to generate corresponding symmetric urea compounds containing different functional groups under mild conditions (100 DEG C, diglyme). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of toxic carbonylation reagents, isocyanate, high-pressure CO2, expensive dehydrating agents and precious metals is avoided, purification and separation ofintermediates are not needed, pure products can be obtained only through simple suction filtration and separation after the reaction is finished, and the method is an efficient and novel synthesis method and has high industrial application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing symmetrical urea compounds. Background technique [0002] Symmetrical urea compounds are a very important class of fine chemicals and important chemical raw materials, and have been widely used in the fields of biological activity research, analytical chemistry, medicinal chemistry, polymer science, agricultural chemistry and organic synthesis (Huang, H.M., McDouall, J.J.W. & Procter, D.J. Angew. Chem. Int. Ed. 2018, 130, 5089–5093; Volz, N. & Clayden, J. Angew. Chem. Int. Ed. 2011, 50, 12148–12155). Therefore, it is of great significance to develop efficient methods for the synthesis of symmetrical urea compounds. [0003] Traditional synthetic methods are usually based on the carbonylation of organic amines / isocyanates with highly toxic carbonylating reagents, for example, phosgene and carbon monoxide (CO) (Huang, X.M., Xu, S.G., Tan, Q., Gao...

AI Technical Summary

Problems solved by technology

Currently reported reaction systems usually require specific metal catalysts, expensive dehydrating agents, and high-pressure CO 2 , especially for aromatic amine substrates (Peterson, S.L., Stucka, S.M. & Dinsmore, C.J.Org. Lett. 2010, 12, 1340-1343; Saylik, D., Horvath, M.J., Elmes, P.S. & Jackson, W.R.J.Org .Chem.1999, 64,3940-3946; Vinogradova,E.V.,Fors,B.P.&Buchwald,S.L.ical ureas.J.Am.Chem.Soc.2012,134,11132-11135;Chen,B.,Peng,J.B.,Ying , J., Qi, X.X. & Wu, X.F. Adv. Synth. Catal. 2018, 360, 2820-2824)

These existing problems greatly limit its large-scale use in industry

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