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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 8
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Original Articles

A Convenient Synthesis of N-Methoxy-N-Methylamides from Carboxylic Acids

Mukund P. Sibi Department of Chemistry, North Dakota State University Fargo, ND, 58105
,
Chad C. Stessman Department of Chemistry, North Dakota State University Fargo, ND, 58105
,
Jeffrey A. Schultz Department of Chemistry, North Dakota State University Fargo, ND, 58105
,
James W. Christensen Department of Chemistry, North Dakota State University Fargo, ND, 58105
,
Jianliang Lu Department of Chemistry, North Dakota State University Fargo, ND, 58105
&
Mali Marvin Department of Chemistry, North Dakota State University Fargo, ND, 58105
Pages 1255-1264 | Received 11 Oct 1994, Published online: 23 Sep 2006

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Fathima Pilathottathil, Doppalapudi Vineet Kumar & Alagiri Kaliyamoorthy. (2020) Synthesis of various acylating agents directly from carboxylic acids. Synthetic Communications 50:11, pages 1622-1632.
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Manju Bala, Praveen Kumar Verma, Neeraj Kumar & Bikram Singh. (2015) Direct Waste-Free Synthesis of Amides from Nonactivated Carboxylic Acids and Amines: Application to the Synthesis of Tetrahydroisoquinolines. Synthetic Communications 45:7, pages 847-856.
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Kieseung Lee, Sang‐Bae Han, Eun‐Mi Yoo, Soon‐Ryang Chung, Haibum Oh & Sungwan Hong. (2004) Efficient Transformation of Aldoximes to Nitriles Using 2‐Chloro‐1‐methylpyridinium Iodide Under Mild Conditions. Synthetic Communications 34:10, pages 1775-1782.
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Misoo Kim, Hagyoung Lee, Ki-Jong Han & Kwang-Yol Kay. (2003) An Efficient One-Pot Synthesis of N-Methoxy-N-methylamides from Carboxylic Acids. Synthetic Communications 33:23, pages 4013-4018.
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Martin Banwell & Jason Smith. (2001) A MILD, ONE-POT METHOD FOR THE CONVERSION OF CARBOXYLIC ACIDS INTO THE CORRESPONDING WEINREB AMIDES. Synthetic Communications 31:13, pages 2011-2019.
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T. Raghuram, S. Vijaysaradhi, Indrapal Singh & Jaimala Singh. (1999) Convenient Conversion of Acid to Weinreb's Amide. Synthetic Communications 29:18, pages 3215-3219.
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Articles from other publishers (28)

Patrick R. Conlon, Venu Reddy Gurijala, Michael Kaufman, Dachang Li, Jiuyuan Li, Yuanyuan Li, Mao Yin, Bollu Satyanarayan Reddy, Thomas Wagler, Zedong Wang, Zhongmin Xu, Aleksandr V. Yurkovetskiy & Lei Zhu. (2022) Process Development and GMP Production of a Conjugate Warhead: Auristatin F-HPA-Ala/TFA (XMT-1864/TFA). Organic Process Research & Development 26:8, pages 2124-2137.
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Jae In Lee & Hyun Park. (2021) Synthetic Approaches to N ‐Methoxy‐ N ‐methylamides . Bulletin of the Korean Chemical Society 42:7, pages 1001-1013.
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Tuan Thanh Dang, Anqi Chen & Abdul Majeed Seayad. (2014) An Efficient synthesis of Weinreb amides and ketones via palladium nanoparticles on ZIF-8 catalysed carbonylative coupling. RSC Adv. 4:57, pages 30019-30027.
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Tanveer Mahamadali Shaikh, Chia-Ming Weng & Fung-E Hong. (2012) Secondary phosphine oxides: Versatile ligands in transition metal-catalyzed cross-coupling reactions. Coordination Chemistry Reviews 256:9-10, pages 771-803.
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Bhavesh H. Patel, Andrew M. Mason, Hetal Patel, R. Charles Coombes, Simak Ali & Anthony G. M. Barrett. (2011) Conversion of α-Amino Acids into Bioactive o -Aminoalkyl Resorcylates and Related Dihydroxyisoindolinones . The Journal of Organic Chemistry 76:15, pages 6209-6217.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 2956 2962 .
Zvi RappoportAndrea Porcheddu & Giampaolo Giacomelli. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Joong-Gon Kim & Doo-Ok Jang. (2010) A Convenient One-Pot Method for the Synthesis of N-Methoxy-N-methyl Amides from Carboxylic Acids. Bulletin of the Korean Chemical Society 31:1, pages 171-173.
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Teng Niu, Weiming Zhang, Danfeng Huang, Changming Xu, Haifeng Wang & Yulai Hu. (2009) A Powerful Reagent for Synthesis of Weinreb Amides Directly from Carboxylic Acids. Organic Letters 11:19, pages 4474-4477.
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A. Deagostino, Paolo Larini, Ernesto G. Occhiato, Lorena Pizzuto, Cristina Prandi & Paolo Venturello. (2008) Synthesis of Weinreb Amides via Pd-Catalyzed Aminocarbonylation of Heterocyclic-Derived Triflates. The Journal of Organic Chemistry 73:5, pages 1941-1945.
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Setsuo Funasaka & Teruaki Mukaiyama. (2008) A Versatile, Practical, and Inexpensive Reagent, Pyridine-3-carboxylic Anhydride (3-PCA), for Condensation Reactions. Bulletin of the Chemical Society of Japan 81:1, pages 148-159.
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. (2007) A Novel Synthesis of N-Methoxy-N-methylamides from 4,6-Pyrimidyl Urethane and Grignard Reagents. Bulletin of the Korean Chemical Society 28:4, pages 695-697.
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. (2005) A New Synthesis of N-Methoxy-N-methylamides from S-2-Pyridyl Thiocarbamate and Grignard Reagents. Journal of the Korean Chemical Society 49:6, pages 609-612.
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Cyrous O. Kangani & David E. Kelley. (2005) One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent. Tetrahedron Letters 46:51, pages 8917-8920.
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So-Yeop Han & Young-Ah Kim. (2004) Recent development of peptide coupling reagents in organic synthesis. Tetrahedron 60:11, pages 2447-2467.
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Kazuhito Hioki, Hiroko Kobayashi, Rumi Ohkihara, Shohei Tani & Munetaka Kunishima. (2004) Preparation of Weinreb Amides Using 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride (DMT-MM). Chemical and Pharmaceutical Bulletin 52:4, pages 470-472.
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Michele Badioli, Roberto Ballini, Massimo Bartolacci, Giovanna Bosica, Elisabetta Torregiani & Enrico Marcantoni. (2002) Addition of Organocerium Reagents to Morpholine Amides:  Synthesis of Important Pheromone Components of Achaea j anata . The Journal of Organic Chemistry 67:25, pages 8938-8942.
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. (2002) An Efficient Synthesis of N-Methoxy-N-methylamides from Carboxylic Acids Using N-Methoxy-N-methylcarbamoyl Chloride. Bulletin of the Korean Chemical Society 23:3, pages 521-525.
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Miguel A Bailén, Rafael Chinchilla, David J Dodsworth & Carmen Nájera. (2001) Direct synthesis of hydroxamates from carboxylic acids using 2-mercaptopyridone-1-oxide-based thiouronium salts. Tetrahedron Letters 42:30, pages 5013-5016.
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Lidia De Luca, Giampaolo Giacomelli & Maurizio Taddei. (2001) An Easy and Convenient Synthesis of Weinreb Amides and Hydroxamates. The Journal of Organic Chemistry 66:7, pages 2534-2537.
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Munetaka Kunishima, Chiho Kawachi, Kazuhito Hioki, Keiji Terao & Shohei Tani. (2001) Formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM. Tetrahedron 57:8, pages 1551-1558.
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Ashok Rao Tunoori, Jonathan M. White & Gunda I. Georg. (2000) A One-Flask Synthesis of Weinreb Amides from Chiral and Achiral Carboxylic Acids Using the Deoxo-Fluor Fluorinating Reagent. Organic Letters 2:25, pages 4091-4093.
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Carme Alemany, Jordi Bach, Jordi Garcia, Marta López & Ana B. Rodrı́guez. (2000) A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones. Tetrahedron 56:47, pages 9305-9312.
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Mei‐Ling Lin, Huey‐Min Wang, Iou‐Jiun Kang & Ling‐Ching Chen. (2013) Ene Reaction with Pummerer‐type Reaction Intermediate of α‐(Methylthio)‐ N ‐methoxy‐ N ‐methyl Acetamide: A New Synthesis of N ‐methoxy‐ N ‐methyl‐( E,E )‐2,4‐dienamides . Journal of the Chinese Chemical Society 47:5, pages 1121-1124.
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Jaimala Singh, N. Satyamurthi & Indrapal Singh Aidhen. (2000) The Growing Synthetic Utility of Weinreb′s Amide. Journal für praktische Chemie 342:4, pages 340-347.
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Masahiro Murakami, Yujiro Hoshino, Hajime Ito & Yoshihiko Ito. (1998) Palladium-Catalyzed Coupling Reactions of N-Methoxy-N-methylcarbamoyl Chloride for the Synthesis of N-Methoxy-N-methylamides. Chemistry Letters 27:2, pages 163-164.
Crossref
Matthew N. Mattson & Henry Rapoport. (1996) A New Method for Expeditious Ketone Synthesis from Acids via Acyl Hemiacetals. The Journal of Organic Chemistry 61:17, pages 6071-6074.
Crossref
M. P. SIBI, C. C. STESSMAN, J. A. SCHULTZ, J. W. CHRISTENSEN, J. LU & M. MARVIN. (2010) ChemInform Abstract: A Convenient Synthesis of N‐Methoxy‐N‐methylamides from Carboxylic Acids.. ChemInform 26:31.
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