53101-94-3

Usage

Uses

Used in Pharmaceutical Industry:
Urea, N-phenyl-N'-(2-pyridinylmethyl)is used as a key intermediate in the synthesis of various pharmaceuticals for its potential medicinal properties. It serves as a precursor in the development of new drugs with anti-inflammatory and anticancer activities, contributing to the advancement of therapeutic options for patients.
Used in Agrochemical Industry:
Urea, N-phenyl-N'-(2-pyridinylmethyl)is utilized as a building block in the production of agrochemicals, such as insecticides and pesticides. Its incorporation into these products enhances their effectiveness in controlling pests and protecting crops, thereby contributing to increased agricultural productivity and food security.
Used in Organic Chemistry Research:
Urea, N-phenyl-N'-(2-pyridinylmethyl)is employed as a valuable building block in organic chemistry research, enabling the development of novel compounds with diverse applications. Its unique structure allows for the exploration of new chemical reactions and the synthesis of innovative molecules with potential uses in various fields, including materials science, environmental science, and medicinal chemistry.

Upstream product

• 3731-51-9 2-(Aminomethyl)pyridine 
• 103-71-9 phenyl isocyanate 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 

Downstream Products

• 87344-94-3 1-nitroso-1-phenyl-3-(2-pyridylmethyl)urea 
• 842-07-9 Sudan I 
• 56395-94-9 N-phenyl-N'-(1-methylpyridinium-2-ylmethyl)urea iodide 
• 80145-75-1 ethyl N-(2-pyridylmethyl)carbamate 
• 62-53-3 aniline 

Relevant academic research and scientific papers

(Thio)urea-catalyzed friedel-crafts reaction: Synthesis of bis(indolyl)-methanes

Bis(indolyl)methane derivatives (BIMs) were synthesized in moderate to good yields by (thio)urea catalyzed electrophilic substitution of indole (2) with various aldehydes 1. Reactions were performed under conventional and microwave (MW) heating, either using 1,2-dichloroetane as solvent or without solvent. The procedure using microwave heating was also applied to the synthesis of the natural products vibrindole A (3n), arsindoline A (3i), arundine (3o) and tris(1H-indol-3-yl)methane (3j). Additionally, the synthesis of streptindole was carried out via intermediate 3g. This methodology is well suited for the synthesis of bis(indolyl)methanes: it offers good yields of products, low sensitivity to moisture and oxygen, high tolerance to different functional groups on the aldehydes such as al-kynes and trimethylsilane, and simplicity in operation

Synthetic method and application of urea compound

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

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.

Synthesis and crystal structure of N-phenyl-N′-(pyridin-2-ylmethyl)-S-methyl-thiouronium iodide

Methylation of N-phenyl-N′-(pyridin-2-ylmethyl)thiourea led to a new low melting thiouronium iodide salt, whereas a further methylation of the nitrogen of the pyridine ring was not successful. This could be explained by the inactivity of the nitrogen atom