13468-02-5Relevant academic research and scientific papers
The solid state structures of ortho-lithio-β-(N,N-dimethylamino)ethoxybenzene and the corresponding sodium compound: A new type of organolithium tetramer and a first example of an organosodium hexamer
Den Besten, Remco,Lakin, Miles T.,Veldman, Nora,Spek, Anthony L.,Brandsma, Lambert
, p. 191 - 196 (1996)
The crystal structures of ortho-lithio-β-(N,N-dimethylamino)ethoxybenzene (2) and the corresponding sodium compound (3) are presented. 2 displays a new type of organolithium tetramer and 3 is the first example of an organosodium hexamer in the solid state
Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols
Bai, Jixiang,Wang, Tianxin,Dai, Botao,Liu, Qingchao,Yu, Peiyuan,Jia, Tiezheng
supporting information, p. 5761 - 5765 (2021/08/16)
A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
supporting information, p. 3459 - 3464 (2021/05/24)
N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
NOVEL COMPOUND, PREPARATION METHOD THEREOF, AND USE THEREOF
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Paragraph 452-456, (2021/07/24)
The present invention relates to a method for preparing a biomaterial having selectively functionalized tyrosine, a biomaterial having selectively functionalized tyrosine, and a pharmaceutical composition containing the same as an active ingredient. The method for preparing a biomaterial to which a compound represented by formula 2 is coupled, of the present invention, allows the compound represented by formula 2 to be selectively coupled, in a high yield in a biomaterial, to tyrosine, which is present on the surface of an aqueous solution such that the coupling thereof to amino acids other than tyrosine does not occur and, when only one tyrosine is present, heterogeneous mixtures are not present and the inherent activity of the biomaterial is maintained, and thus the compound can be effectively used as a pharmaceutical composition containing a biomaterial drug as an active ingredient. In addition, the method can selectively functionalize tyrosine, and thus can be effectively used for tyrosine functionalization in a biomaterial.
Synthesis and characterization of herbicidal ionic liquids based on (4-chloro-2-methylphenoxy)acetate and phenoxyethylammonium
Ciarka, Kamil,Olszewski, Radoslaw,Praczyk, Tadeusz,Pernak, Juliusz
, p. 3607 - 3615 (2021/03/30)
Ten ionic liquids containing the (4-chloro-2-methylphenoxy)acetate (MCPA) anion and domiphen derived phenoxyethylammonium cation were synthesized. The obtained compounds differed in terms of the substitution of the phenoxyethylammonium group in the ring (the presence of a methyl group in the meta or para positions and the presence of chlorine in the para position) as well as the length of the alkyl chain (from hexyl to tetradecyl). The basic physicochemical properties of the obtained ionic liquids (solubility and thermal stability) were characterized and their structures were confirmed. The herbicidal activity of the compounds was tested under greenhouse conditions using cornflower (Centaurea cyanus L.) as the test plant.
Domiphen impurity synthesis method
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Page/Page column 4-6, (2020/08/09)
The invention discloses a domiphen impurity synthesis method. The method comprises the following steps: S1, dissolving phenol in a solvent A, adding a substance B, carrying out heating, carrying out aheat-preserved reaction, dropwise adding a dimethylaminochloroethane solution, carrying out refluxing, and performing purifying to obtain N,N-dimethyl-2-phenoxyethylamine; and S2, subjecting 1-bromotetradecane and the N,N-dimethyl-2-phenoxyethylamine obtained in the step S1 to refluxing in a solvent C, then carrying out crystallizing, and performing drying to obtain brominated N,N-dimethyl-N-(2-phenoxyethyl)-1-tetradecylamine; or subjecting 1-bromodecane and the N,N-dimethyl-2-phenoxyethylamine obtained in the step S1 to refluxing in ethyl acetate, then carrying out crystallizing, and performing drying to obtain brominated N,N-dimethyl-N-(2-phenoxyethyl)-1-decylamine. The method of the invention has the advantages of short synthesis route, mild reaction conditions, few pollutants, high product purity, high yield, economical performance and environmental protection performance.
Preparation method of itopride hydrochloride
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Paragraph 0007; 0014, (2017/01/12)
The invention relates to a preparation method of itopride hydrochloride. The preparation method includes: using 2-dimethylaminoethyl chloride hydrochloride and phenol as starting materials for reaction; subjecting the starting materials to etherification, chloromethylation, amino substitution, amidation and salifying to obtain itopride hydrochloride. Chloromethylation promoted by C/CHO is adopted, so that a step of imine reduction is omitted, solid residue generated by a reductant is eliminated, and reaction safety is improved; raw materials used in the method are low in price, sufficient in market supply and easy to purchase; reaction in each step is classic, and the preparation method is safe, easy to control and suitable for industrial production.
Sulfur and nitrogen mustard carbonate analogues
Arico, Fabio,Chiurato, Matteo,Peltier, Josephine,Tundo, Pietro
experimental part, p. 3223 - 3228 (2012/07/31)
Sulfur and nitrogen half-mustard compounds lose their aggressive properties when the chlorine atom is replaced by a carbonate moiety. The anchimeric effect of the novel mustard carbonate analogues is investigated. The reaction follows first-order kinetics, does not need any base, and occurs with -OH, -NH and acidic -CH nucleophiles. Most of these molecules are unexplored and might provide a novel strategy for the preparation of compounds previously not easily accessible. Copyright
Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology
Hamid, M. Haniti S. A.,Allen, C. Liana,Lamb, Gareth W.,Maxwell, Aoife C.,Maytum, Hannah C.,et al.
supporting information; experimental part, p. 1766 - 1774 (2009/07/25)
The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.
Practical access to amines by platinum-catalyzed reduction of carboxamides with hydrosilanes: Synergy of dual Si-H groups leads to high efficiency and selectivity
Hanada, Shiori,Tsutsumi, Emi,Motoyama, Yukihiro,Nagashima, Hideo
supporting information; experimental part, p. 15032 - 15040 (2010/01/29)
The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions. The rate of the reaction is dependent on the distance of two Si-H groups; 1,1,3,3-tetramethyldisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, CdC, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.
