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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
Further Information
Received
17 March 2009
Publication Date:
29 May 2009 (online)
Publication History
Publication Date:
29 May 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
- 1
Bioorganic
Chemistry of Pesticides
Eto M. Soft Science Publications; Tokyo: 1985. p.73 - 2
Pesticide
Data Book
3rd ed.:
Uesugi Y.Ueji M.Koshioka M. Soft Science Publications; Tokyo: 1997. p.288 - 3
Merck
Index
14th ed.:
O’Neil MJ.Heckelman PE.Koch CB.Roman KJ. Merck & Co., Inc.; Whitehouse Station NJ: 2006. p.6435 - 4
Franz RA.Applegath F. J. Org. Chem. 1961, 26: 3304 - 5
Franz RA.Applegath F.Morriss FV.Baiocchi F. J. Org. Chem. 1961, 26: 3306 - 6
Franz RA.Applegath F.Morriss FV.Baiocchi F.Bolze C. J. Org. Chem. 1961, 26: 3309 - 7
Franz RA.Applegath F.Morriss FV.Baiocchi F.Breed LW. J. Org. Chem. 1962, 27: 4341 - 8
Macho V.Kralik M.Ligac G.Bojsova E.Vojcek L. Collect. Czech. Chem. Commun. 1996, 61: 381 - 9
Wang X.Lu S. J. Mol. Catal. 2006, 255: 25 - 10
Yang Y.Lu S. Tetrahedron Lett. 1999, 40: 4845 - 11
Mizuno T.Iwai T.Ishino Y. Tetrahedron 2005, 61: 9157 - 12
Mizuno T.Mihara M.Iwai T.Ito T.Ishino Y. Synthesis 2006, 2825 - 13
Mizuno T.Nakai T.Mihara M. Heteroat. Chem. 2009, 20: 64 - 14
Mizuno T.Daigaku T.Nishiguchi I. Tetrahedron Lett. 1995, 36: 1533 - 15
Ozaki S.Nagoya T. Bull. Chem. Soc. Jpn. 1957, 30: 444 - 16
Lee S.-H.Matsushita H.Clapham B.Janda KD. Tetrahedron 2004, 60: 3439 - 17
Hoffmann RW.Hagenbruch B.Smith DM. Chem. Ber. 1977, 110: 23 - 18
Henry RA.Dehn WM. J. Am. Chem. Soc. 1949, 71: 2297