- METHOD FOR PRODUCING IMIDAZOLINE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing an imidazoline compound having high yield and small amount of impurity. SOLUTION: There is provided a method for producing an imidazoline compound (B) using a diamine monoamide compound (A) represented by the general formula (1), wherein the method includes a dehydration condensation step of the diamine monoamide compound (A) and a distillation step of the imidazoline compound (B). In the dehydration condensation step, the temperature of the dehydration condensation reaction of (A) is 100°C to 160°C in a time of 50% or more of the process time from when the conversion rate from (A) to (B) becomes 55% until when the conversion rate from (A) to (B) becomes 70%, and a the gas-phase pressure at the temperature of the dehydration condensation reaction of (A) is P1 which satisfies the conditions 1. In the distillation step, the temperature of the liquid containing (A) and (B) is 100°C to 190°C in a time of 50% or more of the process time from when 30 wt.% of the total distillate of (B) is distillated until when 90 wt.% of the total distillate of (B) is distillated, and a pressure (B) in the gas-phase of the distillation step is P2 which satisfies the condition 2. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0045; 0049-0051; 0059-0066; 0069-0070
(2021/06/04)
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- INTRACELLULAR DELIVERY VEHICLE
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PROBLEM TO BE SOLVED: To provide a vehicle which can easily deliver a desired component or compound into a cell without preventing cell proliferation. SOLUTION: A intracellular delivery vehicle has its surface covered with positive electric charge. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0166; 0170-0171
(2020/08/13)
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- INTRACELLULAR DELIVERY VEHICLE
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An intracellular delivery vehicle of which surface is covered by a positive charge, an intracellular delivery complex in which a component or compound desired is loaded in the intracellular delivery vehicle, a temperature-sensitive probe comprising the intracellular delivery complex, and a method for measuring the intracellular temperature by the temperature-sensitive probe are disclosed. The intracellular delivery vehicle is useful on account of its capability of easily delivering the component or compound desired inside the cell without inhibiting cell proliferation.
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Paragraph 0292
(2019/05/18)
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- A Cell-Targeted Non-Cytotoxic Fluorescent Nanogel Thermometer Created with an Imidazolium-Containing Cationic Radical Initiator
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A cationic fluorescent nanogel thermometer based on thermo-responsive N-isopropylacrylamide and environment-sensitive benzothiadiazole was developed with a new azo compound bearing imidazolium rings as the first cationic radical initiator. This cationic fluorescent nanogel thermometer showed an excellent ability to enter live mammalian cells in a short incubation period (10 min), a high sensitivity to temperature variations in live cells (temperature resolution of 0.02–0.84 °C in the range 20–40 °C), and remarkable non-cytotoxicity, which permitted ordinary cell proliferation and even differentiation of primary cultured cells.
- Uchiyama, Seiichi,Tsuji, Toshikazu,Kawamoto, Kyoko,Okano, Kentaro,Fukatsu, Eiko,Noro, Takahiro,Ikado, Kumiko,Yamada, Sayuri,Shibata, Yuka,Hayashi, Teruyuki,Inada, Noriko,Kato, Masaru,Koizumi, Hideki,Tokuyama, Hidetoshi
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supporting information
p. 5413 - 5417
(2018/04/09)
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- Colloid and nanosized catalysts in organic synthesis: XIII. Synthesis of 2-R-2-imidazolines catalyzed by copper and iron oxide nanoparticles
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The reaction of carboxylic acids with ethylenediamine catalyzed by copper or iron oxide nanoparticles proceeds at 80°C with azeotropic water distilling off during 2-8 h to form 2-R-2-imidazolines. Acyl and diacyl derivatives of ethylenediamine are formed in the reaction as side products.
- Popov,Mokhov,Kalitina
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p. 281 - 285
(2016/04/20)
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- Push-pull alkenes by reacting N,N′-dimethyl cyclic ketene N,N′-acetals with isocyanates: synthesis, structures, and reactivities
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N,N′-Dimethyl cyclic ketene N,N′-acetals react with two or three equivalents of isocyanates to generate tetrasubstituted push-pull alkene derivatives in one-pot sequential reactions. X-ray crystallography showed significant elongations and out of plane distorsions of the polarized carbon-carbon double bonds.
- Ye, Guozhong,Henry, William P.,Chen, Chunlong,Zhou, Aihua,Pittman Jr., Charles U.
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supporting information; experimental part
p. 2135 - 2139
(2009/07/26)
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- Easy access to triazoles, triazolopyrimidines, benzimidazoles and imidazoles from imidates
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We have described a new and easy synthesis of triazoles, triazolopyrimidines, benzimidazoles and imidazoles variously substituted based on the reaction of imidates with diamine derivatives. The products were obtained in moderate to good yields. A general mechanism for the reactions is proposed.
- Zarguil,Boukhris,El Efrit,Souizi,Essassi
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body text
p. 5883 - 5886
(2009/04/05)
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- Synthesis of aldehydes from carboxylic acids via 2-imidazolines
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The use of readily available 2-substituted-2-imidazolines as precursors to 2-hydroxy aldehyde, unsaturated aldehyde and a variety of functionalized aldehydes is reported. It provides a novel method for the preparation of aldehydes from carboxylic acids via 2-substituted-2-imidazolines.
- Shi, Zhen,Gu, Huan
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p. 2701 - 2707
(2007/10/03)
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- The mechanisms of the formation of by-products in the catalytic synthesis of C-alkylimidazoles from diamines and carboxylic acids
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The formation of 1-ethyl-2-methylimidazole (1-Et-2-MI) and 1-ethyl-2-methylimidazoline (1-Et-2-MIN), intermediates in the synthesis of 2-methylimidazole (2-MI) from ethylenediamine (EDA) and AcOH in the presence of a platinum-on-alumina catalyst, was studied.Using CH3(14)COOH the incorporation of two acetate units into 1-Et-2-MI and 1-Et-2-MIN molecules was demonstrated.The same products were also obtained on dehydrogenation of 2-methylimidazoline (2-MIN) under mild conditions (220-230 deg C).A part of the latter is transformed to N-ethyl ethylendiamine (EEDA) and EDA.These facts indicate that both 1-Et-2-MI and 1-Et-2-MIN result from hydrogenolysis of the imidazoline ring with subsequent ethylation.A reverse reaction, the C5-cyclization of EEDA, was also observed.The formation of 2-MI is favored by increasing temperature.
- Gitis, K. M.,Raevskaya, N. I.,Isagulyants, G. V.
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p. 895 - 898
(2007/10/02)
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- Copper(I)-induced addition of amines to unactivated nitriles: The first general one-step synthesis of alkyl amidines
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Cu(I)Cl promotes the condensation of acetonitrile 1a and benzonitrile 1b with primary and secondary amines 2a-g into amidines 3a-j under mild conditions, in high to quantitative yields. Stoichiometric formation of Cu(I)-amidines complexes allows to control the degree of substitution of resulting amidines.
- Rousselet,Capdevielle,Maumy
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p. 6395 - 6398
(2007/10/02)
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- THE STAGED SYNTHESIS OF 2-METHYLIMIDAZOLE FROM ETHYLENEDIAMINE AND ACETIC ACID IN THE PRESENCE OF A BIFUNCTIONAL ALUMINOPLATINUM CATALYST
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An investigation has been conducted into the staged synthesis of 2-methylimidazole from ethylenediamine and acetic acid in the presence of a bifunctional aluminoplatinum catalyst.It has been shown that the formation stage of 2-methylimidazoline occurs more quickly on γ-Al2O3 than its dehydrogenation on the Pt centers.From a comparison of the processes of dehydrogenation of 2-methylimidazoline in the molten phase and in aqueous solution it follows that the water eliminated in the imidazoline formation stage could cause the decrease in activity during the dehydrogenation on the Pt centers.The structures of the secondary and intermediate products have been established for each stage of the process and their formation routes are discussed. Keywords: aluminoplatinum catalysts, bifunctional catalysis, alkylimidazoles, 2-methylimidazole.
- Gitis, K. M.,Raevskaya, N. I.,Isagulyants, G. V.
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p. 1551 - 1554
(2007/10/02)
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- CATALYTIC SYNTHESIS OF C-ALKYLIMIDAZOLES OVER PLATINUM-ALUMINA CATALYSTS
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The synthesis of C-alkylimidazoles from 1,2-diamines and carboxylic acids over bifunctional platinum-alumina catalysts has been studied.It has been shown that this method is effective for the synthesis of 2-alkyl and 2,4-dialkylimidazoles including imidazoles with long-chain alkyls.The effect of the reaction temperature, space velocity of the flow of the raw materials, and dilution by hydrogen on the yield of product has been examined for the example of the synthesis of 2-methylimidazole from ethylenediamine and acetic acid, and the stability of the catalyst in continuous reaction cycles with intermediate oxidative regeneration has been studied.The composition of the accompanying products has been established and a mechanism proposed for their formation.Keywords: bifunctional catalyst, platinum-alumina catalyst, alkylimidazoles, 2-methylimidazole.
- Gitis, K. M.,Neumoeva, G. E.,Raevskaya, N. I.,Arutyunyants, G. A.,Isagulyants, G. V.
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p. 728 - 734
(2007/10/02)
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- EFFECT OF THE SURFACE AREA OF PLATINUM ON THE ACTIVITY OF A BIFUNCTIONAL ALUMINOPLATINUM CATALYST IN THE SYNTHESIS OF ALKYLIMIDAZOLES FROM DIAMINES AND CARBONYL ACIDS
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An investigation has been conducted into the effect of the acid and dehydrogenating functions of an aluminoplatinum catalyst on the synthesis of 2-methylimidazole from ethylenediamine and acetic acid.It has been established that formation of the intermediate 2-methylimidazoline involves the acid Al2O3 centers and its rate of formation is greater than the rate of its subsequent dehydrogenation to 2-methylimidazole on the Pt centers.The symbatic nature of the variations in the 2-methylimidazole yield and the surface area of the platinum in the aluminoplatinum catalyst has been demonstrated.Keywords: C-alkylimidazoles, 2-methylimidazole, aluminoplatinum catalyst.
- Gitis, K. M.,Raevskaya, N. I.,Zaitsev, A. V.,Borovkov, V. Yu.,Kozan, S. B.,Isagulyants, G. V.
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p. 1547 - 1550
(2007/10/02)
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- 1,2- and 1,3-Diamine Exchange between Substituted 4,5-Dihydroimidazoles and 1,4,5,6-Tetrahydropyrimidines: Routes to Benzimidazoles, Dihydroimidazoles, and Tetrahydropyrimidines
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A range of 2-substituted 4,5-dihydroimidazoles and 2-substituted 1,4,5,6-tetrahydropyrimidines when heated with an excess of substituted ethane-1,2-diamines, o-phenylenediamines, and propane-1,3-diamine underwent diamine exchange to give 2-substituted heterocycles derived from the solvent diamine.The reaction was an equilibrium process favouring six-membered rings.The synthetic scope is amplified by the ready aromatisation of these partially reduced heterocycles.
- Butler, Richard N.,Fitzgerald, Kevin J.
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p. 155 - 157
(2007/10/02)
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- Manufacture of 2-oxazolines, 2-oxazines, 2-imidazolines and 2-imidazines
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A process for the production of a product selected from the group consisting of a 2-oxazoline or a 2-oxazine and a 2-imidazoline or a 2-imidazine comprising reacting a bicyclic amide acetal with a member selected from the group consisting of an alkanol amine and an alkylene polyamine, respectively, at a temperature in the range of from about 20° C. to 200° C. is described.
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- Use of Lanthanide(III) Ions as Catalysts for the Reactions of Amines with Nitriles
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Catalytic amounts of lanthanide(III) triflates promote reactions between amines and nitriles leading to a variety of products.The Ln3+ ions activate weakly coordinating nitriles at large amine: Ln3+ mole ratios, even in the presence of amines that form thermodynamically stable complexes with Ln3+ ions.The reactions involving primary monoamines and diamines appear to be general and provide a viable synthetic route to N,N'-disubstituted amidines (2) and cyclic amidines (4), respectively.Symmetrically substituted triazines (8 or 9) are observed as byproducts in some of these systems when the reactions are carried out by using excess nitrile.Secondary alicyclic amines or dimethylamine reacts with acetonitrile to yield pyrimidines (6) and 2,4,6-trimethyl-s-triazine (8).Two routes to triazine have been proposed, one involving the reaction of ammonia with the nitrile and the second involving the reaction of an amidine (1 or 5) with the nitrile.The ability of Ln3+ ions to activate nitriles under conditions that oppose nitrile coordination is attributed to the lability of Ln3+ complexes derived from N-donors.
- Forsberg, John H.,Spaziano, Vincent T.,Balasubramanian, Trichey M.,Liu, Gordon K.,Kinsley, Steven A.,et al.
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p. 1017 - 1021
(2007/10/02)
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- REACTIONS OF TRIVALENT PHOSPHORUS COMPOUNDS WITH AZIDES CONTAINING A MOBILE H-ATOM. A CONCEPTION OF PHOSPHAZO-COMPOUND SPIROCYCLIZATION MECHANISM
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Investigation of the reactions of α-azidocarboxylic acids, N-(2-azidoethyl)amides and N-(2-azidoethyl)amines with trivalent P compounds shows that the intramolecular cyclization to spirophosphoranes of the intermediate phosphazo-compounds is typical of the azides of the first and third types but not of the second type.It is concluded that such cyclization is possible only where the functional group of the starting azides contains either a sufficiently mobile hydrogen atom or a highly nucleophilic proton-containing group.A new general process for producing imidazolines and oxazolines has been developed.
- Gololobov, Yu G.,Gusar, N. I.,Chaus, M. P.
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p. 793 - 800
(2007/10/02)
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- Preparation of 2-imidazolines
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A novel process for the preparation of 2-imidazolines by reacting 1,2-diamines with nitriles or carbonyl compounds in the gas phase at from 200° to 450° C. in the presence of an oxide or phosphate of a metal of group 3 or 4 of the periodic table and/or in the presence of silicon dioxide. The 2-imidazolines obtainable by the process of the invention are valuable starting materials for the preparation of dyes, crop protection agents and drugs.
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