70657-67-9Relevant academic research and scientific papers
A direct and mild conversion of tertiary aryl amides to methyl esters using trimethyloxonium tetrafluoroborate: A very useful complement to directed metalation reactions
Keck, Gary E,McLaws, Mark D,Wager, Travis T
, p. 9875 - 9883 (2000)
The scope and generality of a direct process for the conversion of tertiary amides directly to methyl esters has been investigated. The process involves a two-step, one pot procedure in which a tertiary amide is first treated with trimethyloxonium tetrafluoroborate to generate an imidate intermediate which is then hydrolyzed, generally by the addition of saturated aqueous sodium bicarbonate solution. Although this process fails for aliphatic amides, very good yields are realized for a variety of amides derived from aromatic carboxylic acids. Steric hindrance at the N-alkyl group is well tolerated; thus N,N-dimethyl, -diethyl, and -diisopropyl amides can all be utilized successfully. (C) 2000 Elsevier Science Ltd.
Metal-Free Amidation of Acids with Formamides and T3P
Bannwart, Linda,Abele, Stefan,Tortoioli, Simone
, p. 2069 - 2078 (2016/07/06)
A new, simple and metal-free method for the direct formation of dialkylamides from carboxylic acids employing N,N-dialkylformamides as amine source is described. The one-pot reaction is promoted by propylphosphonic anhydride (T3P) in the presence of 0.5 equivalents of HCl.
