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A Convenient Synthesis of 2-Methoxycarbonyl-5-iodobenzene Sulfonamide
Corresponding Author(s) : Defeng Xu
Asian Journal of Chemistry,
Vol. 29 No. 7 (2017): Vol 29 Issue 7
Abstract
A convenient and concise synthesis of 2-methyl-5-nitrobenzene sulfonamide can be achieved by sulfochlorination and ammoniation with p-nitrotoluene as raw materials for an 81.2 % yield. 6-Aminosaccharin can be produced via oxidation and reduction in a 64.3 % yield and then the iodination using potassium iodide can afford 6-iodosaccharin with a 70.8 % yield. 2-Methoxycarbonyl-5-iodobenzene sulfonamide can be produced via esterification in a 94.1 % yield.
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- J.S. Liu, J.J. Kou and G.L. Liu, Agrochemicals, 46, 145 (2007).
- D. J. Nevill and C. H. Riehen, Broad-Spectrum Pre- or Post=Emergence Herbicidal Composition, Patent-DE19834627A (1983).
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- H.C. Li, K. Sun and M.H. Zhang, Agrochemicals, 53, 227 (2014).
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- J. Diao and F. Ao, Agrochemicals, 46, 484 (2007).
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- A. Warren and G.H. Hamor, J. Pharm. Sci., 50, 625 (1961); https://doi.org/10.1002/jps.2600500723.
- L. Han, L. Wang, X. Hou, H. Fu, W. Song, W. Tang and H. Fang, Med. Chem., 22, 1529 (2014); https://doi.org/10.1016/j.bmc.2014.01.045.
- N. Gençer, D. Demir, F. Sonmez and M. Kucukislamoglu, Med. Chem., 20, 2811 (2012); https://doi.org/10.1016/j.bmc.2012.03.033.
References
J.S. Liu, J.J. Kou and G.L. Liu, Agrochemicals, 46, 145 (2007).
D. J. Nevill and C. H. Riehen, Broad-Spectrum Pre- or Post=Emergence Herbicidal Composition, Patent-DE19834627A (1983).
M. Witschel, C. Zagar and A. Landes, Synergistically Acting Herbicidal Mixtures, Patent-ZA200508237(B)(2005).
R. Hain, G. Johann and U. Bickers, Use of Als Inhibitor Herbicides for Control of Unwanted Vegetation in Als Inhibitor Herbicide Tolerant Brassica, Such As B. Napus, Plants, Patent WO2012150333(A1) (2012).
L. Xu, H. Shu, Y. Liu and M. Trudell, ChemInform, 62, 7902 (2006); https://doi.org/10.1016/j.tet.2006.05.038.
H.C. Li, K. Sun and M.H. Zhang, Agrochemicals, 53, 227 (2014).
O. Ort, K. Bauer and H. Bieringer, Arylsulfonylureas, Processes for their Preparation and their use as Herbicides and Growth Regulators, Patent US5463081A1 (1995).
J. Diao and F. Ao, Agrochemicals, 46, 484 (2007).
Z. Wang, F. Kong and Z. Cao, J. Suzhou Univ., 25, 66 (2009).
H. Kamogawa, S. Yamamoto and M. Nanasawa, Bull. Chem. Soc. Jap., 55, 3824 (1982); https://doi.org/10.1246/bcsj.55.3824.
H. Zhang, C. Yang, W. Lu, J. Huang, W. Zhu, H. Li, Y. Xu and X. Qian, Chem. Commun., 47, 8301 (2011); https://doi.org/10.1039/c1cc12386f.
A. Warren and G.H. Hamor, J. Pharm. Sci., 50, 625 (1961); https://doi.org/10.1002/jps.2600500723.
L. Han, L. Wang, X. Hou, H. Fu, W. Song, W. Tang and H. Fang, Med. Chem., 22, 1529 (2014); https://doi.org/10.1016/j.bmc.2014.01.045.
N. Gençer, D. Demir, F. Sonmez and M. Kucukislamoglu, Med. Chem., 20, 2811 (2012); https://doi.org/10.1016/j.bmc.2012.03.033.