10264-11-6Relevant articles and documents
(Chloro-phenylthio-methylene)dimethylammonium chloride (CPMA): A new coupling reagent for the formation of ester and amide bond
Gomez, Laurent,Ngouela, Silvère,Gellibert, Fran?oise,Wagner, Alain,Mioskowski, Charles
, p. 7597 - 7599 (2002)
CPMA is an efficient agent for the formation of esters and amides from carboxylic acids. It is compatible with substrates that are sensitive to basic conditions or oxophilic reagents. The reaction proceeds without racemization of chirally labile carboxylic acids. All these advantages make CPMA a valuable adjunct to the existing arsenal of coupling reagents.
Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
, p. 2820 - 2826 (2021/02/01)
A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.
PRODUCTION METHOD OF AMIDE COMPOUND
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Paragraph 0018; 0112-0120; 0123-0126, (2020/10/08)
PROBLEM TO BE SOLVED: To provide a production method of an amide compound, which can use a variety of carboxylic acid halides and can produce a desired amide compound at a yield higher than a batch process by suppressing a side reaction. SOLUTION: Provided is a production method of an amide compound using a flow type reactor, in which the flow type reactor includes: a first flow path; a second flow path; a first mixing means provided at a confluent part of the first flow path and the second flow path; and a third flow path that is connected to the first mixing means and arranged on a down stream side of the first mixing means, the production method comprising: a mixing step of obtaining a mixed liquid by circulating a first liquid containing the carboxylic acid halide in the first flow path, circulating a second liquid containing an amine compound having a molecular weight of 1,000 or less, an inorganic alkali and water in the second flow path, and mixing the first liquid and the second liquid by the first mixing means to obtain a mixture; and a reaction step of obtaining an amide compound by circulating the mixed liquid in the third flow path and reacting the carboxylic acid halide and the amine compound in the third flow path. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPO&INPIT
Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
supporting information, p. 5098 - 5102 (2018/09/13)
An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
