Formation of Acrylanilides, Acrylamides, and Amides Directly from Carboxylic Acids Using Thionyl Chloride in Dimethylacetamide in the Absence of Bases

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• 作者：Raymond J. Cvetovich ; Lisa DiMichele
• 刊名：Organic Process Research & Development
• 出版年：2006
• 出版时间：September 2006
• 年：2006
• 卷：10
• 期：5
• 页码：944 - 946
• 全文大小：53K
• 年卷期：v.10,no.5(September 2006)
• ISSN：1520-586X

文摘

A general one-pot procedure is described that rapidly convertsacrylic acid to anilides upon sequential treatment of the acidin dimethylacetamide (DMAC) with thionyl chloride andstoichiometric amounts of anilines in 88-98% yields, withDMAC offering rate and stability advantages over the use ofDMF. The use of DMAC was extended to other organic acidsin forming anilides. Benzylamine amides can also be formedusing stoichiometric amounts of benzylamine and brought tocompletion by warming in the absence of additional base. Inaddition, it was shown that tert-butylamides can be easilyformed with the addition of excess tert-butylamine at 20 C.