Low-temperature synthesis of tetraalkylureas from secondary amines and carbon dioxide

Chih-Cheng Tai; Melissa J Huck; Erin P McKoon; Tiffany Woo; Philip G Jessop

doi:10.1021/jo026369j

Low-temperature synthesis of tetraalkylureas from secondary amines and carbon dioxide

J Org Chem. 2002 Dec 13;67(25):9070-2. doi: 10.1021/jo026369j.

Authors

Chih-Cheng Tai¹, Melissa J Huck, Erin P McKoon, Tiffany Woo, Philip G Jessop

Affiliation

¹ Department of Chemistry, University of California-Davis, 95616, USA. [email protected]

PMID: 12467430
DOI: 10.1021/jo026369j

Abstract

The reaction of dialkylamines with CO(2) giving tetraalkylureas can be performed at 60 degrees C. The reaction requires CCl(4), is weakly promoted by DMAN or PPh(3), and is not promoted by a Pd catalyst. A two-step procedure, in which dialkylammonium dialkylcarbamate is produced in situ and then reacted with CCl(4) and free dialkylamine, gave greater yields of urea than a simple single-stage procedure.