53101-94-3Relevant articles and documents
Synthetic method and application of urea compound
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Paragraph 0163-0166, (2019/06/07)
The invention relates to a synthetic method of a urea compound, comprising the following steps: adding substituted oxazolone and sodium acetate into a methanol solution, and adding substituted amine under the stirring condition, reacting and carrying out column chromatography to obtain the urea compound. The defect that dangerous compounds need to be used during existing synthetic process is overcome, and a one-pot method is adopted to replace an existing reaction with low yield. The method of the invention has mild reaction condition, the operation is simple, raw materials are easily available, and the substrate can be converted into various other useful molecules. The compound has strong practicality, and can be applied to synthesis of the pesticide daimuron, dieresis long and the anti-cancer drug Sorafenib. The invention relates to a green and environmentally-friendly unsymmetrical urea compound synthesis method with simple process and low cost.
Cu(II)-ion-catalyzed solvolysis of N,N- bis(2-picolyl)ureas in alcohol solvents: Evidence for cleavage involving nucleophilic addition and strong assistance of bis(2-picolyl)amine leaving group departure
Belzile, Mei-Ni,Neverov, Alexei. A.,Brown, R. Stan
, p. 7916 - 7925 (2014/08/18)
The kinetics and products for solvolysis of N-p-nitrophenyl-N′, N′-bis(pyridin-2-ylmethyl) urea (7a), N-methyl-N-p-nitrophenyl-N′, N′-bis(pyridin-2-yl methyl) urea (7b), and N-phenyl-N′,N′- bis(pyridin-2-yl-methyl) urea (DPPU) (7c) promoted by Cu(II) ion in methanol and ethanol were studied under sspH-controlled conditions at 25 °C. Methanolysis and ethanolysis of these substrates proceeds rapidly at a 1:1 ratio of substrate:metal ion, the half-times for decomposition of the Cu(II):7a complexes being ～150 min in methanol and 15 min in ethanol. In all cases, the reaction products are the Cu(II) complex of bis(2-picolyl)amine and the O-methyl or O-ethyl carbamate of the parent aniline, signifying that the point of cleavage is the bis(2-picolyl) - N - C - O bond. Reactions of the Cu(II):7b complexes in each solvent proceed about 3-5 times slower than their respective Cu(II):7a complexes, excluding an elimination mechanism that proceeds through an isocyanate which subsequently adds alcohol to give the observed products. The reactions also proceed in other solvents, with the order of reactivity ethanol > methanol >1-propanol >2-propanol > acetonitrile (with 0.2% methanol) > water spanning a range of 150-fold. The mechanism of the reactions is discussed, and the reactivity and mode of cleavage are compared with that of the M(II)-promoted ethanolytic cleavage of a mono-2-picolyl derivative, N-p-nitrophenyl-N′-(pyridin-2-yl-methyl) urea (4a), which had previously been shown to cleave at the aniline N-C - O bond. The large estimated acceleration of the rate of attack of ethoxide on 7b of at least 2 × 1016 provided by associating Cu(II) with the departing group in this urea is discussed in terms of a trifunctional role for the metal ion involving Lewis acid activation of the substrate, intramolecular delivery of a Cu(II)-coordinated ethoxide, and metal-ion-assisted leaving group departure.
