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Synthesis 2007(20): 3135-3140
DOI: 10.1055/s-2007-990793
DOI: 10.1055/s-2007-990793
PAPER
© Georg Thieme Verlag Stuttgart · New York
Solvent-Free Synthesis of Urea Derivatives from Primary Amines and Sulfur under Carbon Monoxide and Oxygen at Atmospheric Pressure
Further Information
Received
28 June 2007
Publication Date:
21 September 2007 (online)
Publication History
Publication Date:
21 September 2007 (online)
Abstract
A solvent-free carbonylation and oxidation system aimed at green and sustainable chemistry was developed. With these reactions, an environmentally benign synthesis of urea derivatives could be carried out in good to excellent yields from primary amines and sulfur at ambient pressure of carbon monoxide and oxygen. For example, N,N′-dioctylurea was prepared in 99% yield from two equivalents octylamine and one equivalent sulfur in the presence of carbon monoxide (1 atm) at 80 °C and oxygen (1 atm) at room temperature, in the complete absence of solvent.
Key words
urea derivatives - carbon monoxide - oxygen - sulfur - solvent-free
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Franz RA.Applegath F. J. Org. Chem. 1961, 26: 3304 - 2
Franz RA.Applegath F.Morriss FV.Baiocchi F. J. Org. Chem. 1961, 26: 3306 - 3
Franz RA.Applegath F.Morriss FV.Baiocchi F.Bolze C. J. Org. Chem. 1961, 26: 3309 - 4
Mizuno T.Matsumoto M.Nishiguchi I.Hirashima T. Heteroat. Chem. 1993, 4: 455 - 5
Mizuno T.Iwai T.Ishino Y. Tetrahedron 2005, 61: 9157 - 6
Mizuno T.Mihara M.Iwai T.Ito T.Ishino Y. Synthesis 2006, 2825 - 7
Hailes HC. Org. Process Res. Dev. 2007, 11: 114 - 8
Rayner CM. Org. Process Res. Dev. 2007, 11: 121 - 9
Avalos M.Babiano R.Cintas P.Jiménez JL.Palacios JC. Angew. Chem. Int. Ed. 2006, 45: 3904 - 10
Mizuno T.Iwai T.Ishino Y. Tetrahedron Lett. 2004, 45: 7073 - 11
Mizuno T.Mihara M.Nakai T.Iwai T.Ito T. Synthesis 2007, 2524 - 12
Mizuno T.Daigaku T.Nishiguchi I. Tetrahedron Lett. 1995, 36: 1533 - 13 In the previous report on urea synthesis from primary amines and carbon monoxide in the presence of a selenium catalyst, the same reaction pathway was suggested:
Sonoda N. Pure Appl. Chem. 1993, 65: 699 - 14
Farlow MW.Adkins H. J. Am. Chem. Soc. 1935, 57: 2222 - 15
Boivin PA.Bridgeo W.Boivin JL. Can. J. Chem. 1954, 32: 242 - 16
Mizuno T.Takahashi J.Ogawa A. Tetrahedron 2003, 59: 1327