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Synthesis 2009(15): 2492-2496
DOI: 10.1055/s-0029-1216863
DOI: 10.1055/s-0029-1216863
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Unsymmetrical Ureas by Sulfur-Assisted Carbonylation with Carbon Monoxide and Oxidation with Molecular Oxygen under Mild Conditions
Weitere Informationen
Received
17 March 2009
Publikationsdatum:
29. Mai 2009 (online)
Publikationsverlauf
Publikationsdatum:
29. Mai 2009 (online)
Abstract
With ambient pressure of carbon monoxide and oxygen at room temperature, N,N-dialkyl-N′-arylureas were selectively accessible from secondary amines, aromatic amines, and sulfur in good to excellent yields. For example, N-butyl-N-methyl-N′-(3,4-dichlorophenyl)urea, which is used as a herbicide (neburon), was afforded successfully from butylmethylamine (2 equiv), 3,4-dichloroaniline (1 equiv) and sulfur (1 equiv) in 79% (21.8 g) yield using carbon monoxide (0.1 MPa) and oxygen (0.1 MPa) at 20 ˚C in DMF.
Key words
unsymmetrical ureas - carbon monoxide - oxygen - sulfur - herbicide
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