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Synlett 2006(8): 1161-1164  
DOI: 10.1055/s-2006-926254
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient Sulfur-Catalyzed Oxidative Carbonylation of Primary Amines and β-Amino Alcohols

Xingao Peng, Fuwei Li, Chungu Xia*
State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, and Graduate School of the Chinese Academy of Sciences, Lanzhou, 730000 Gansu, P. R. of China
Fax: +86(931)8277088; e-Mail: cgxia@lzb.ac.cn;
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Publication History

Received 6 November 2005
Publication Date:
10 March 2006 (online)

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Abstract

A highly efficient sulfur-catalyzed oxidative carbonyl­ation of aliphatic amines and aliphatic β-amino alcohols to ureas and 2-oxazolidinones, respectively, was developed. Sodium nitrite was involved in the reoxidation of hydrogen sulfide to sulfur in the ­catalytic oxidative carbonylation cycle.

Key words

sulfur - oxidative carbonylation - amine - β-aminoalcohol - catalysis

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General Experimental Procedure. All oxidative carbonylation experiments were carried out in a 100 mL autoclave equipped with magnetic stirring and automatic temperature control. The amine or ethanolamine (20 mmol), sulfur (1 mmol), NaNO2 (10 mmol), and MeOH (6 mL) were charged into the reactor. Then, the autoclave was flushed three times with CO and pressurized with CO to a pressure of 40 atm. The autoclave was placed in oil bath that was preheated to 120 °C, and the whole reaction mixture was stirred for 10 h. After the reaction, the autoclave was cooled, excess gas was purged, and the reaction mixture was filtered. Qualitative analyses were conducted with a HP 6890/5973 GCMS and quantitative analyses were carried out over a Agilent 6820 GC (FID detector).