15907-76-3Relevant academic research and scientific papers
Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene
Bousfield, Thomas W.,Pearce, Katharine P. R.,Nyamini, Simbarashe B.,Angelis-Dimakis, Athanasios,Camp, Jason E.
supporting information, p. 3675 - 3681 (2019/07/09)
Cyrene as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.
Mild decarboxylative activation of malonic acid derivatives by 1,1′-carbonyldiimidazole
Lafrance, Danny,Bowles, Paul,Leeman, Kyle,Rafka, Robert
supporting information; experimental part, p. 2322 - 2325 (2011/06/26)
Chemical equations presented. Malonic acid derivatives undergo unusually mild decarboxylation when treated with N,N′-carbonyldiimidazole (CDI) at room temperature to generate the carbonyl imidazole moiety in high yield, which can be reacted further with a variety of nucleophiles in an efficient one-pot process.
Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral
Gustafsson, Tomas,Ponten, Fritiof,Seeberger, Peter H.
, p. 1100 - 1102 (2008/09/21)
A safe, functional-group-tolerant and high-throughput version of the trimethylaluminium mediated amide bond formation reaction has been developed in a microreactor system; rimonabant and efaproxiral were prepared to illustrate the utility of the method. The Royal Society of Chemistry.
Kinetics and mechanism of aminolysis of aryl cyclobutane-carboxylates in acetonitrile
Lee, Hai Whang,Yun, You-Sun,Lee, Bon-Su,Koh, Han Joong,Lee, Ikchoon
, p. 2302 - 2305 (2007/10/03)
The aminolysis of Z-aryl cyclobutanecarboxylates (II) with X-benzylamines is investigated in acetonitrile at 55.0 °C. The rates are uniformly greater by 2.2 times than the corresponding rates of aryl cyclopropanecarboxylates (III). All the selectivity par
