- CoFe2O4?SiO2-NH-βCD-BF3 as a supramolecular nanocomposite: Synthesis, characterization and catalytic activity
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This manuscript describes synthesis of BF3-functionlized β-cylcodextrine grafted magnetic CoFe2O4 nanaoparticles as a hybrid magnetic nano-composite (CoFe2O4?SiO2-NH-βCD-BF3). The CoFe2O4?SiO2-NH-βCD-BF3 was fabricated by grafting of 6-O-toluenesulfonyl cyclodextrin (6-Ts-βCD) to 3-aminopropyl triethoxysilane coated magnetic CoFe2O4?SiO2 nanoparticles followed by combination with BF3. The CoFe2O4?SiO2-NH-βCD-BF3was characterized by FT-IR, TGA, VSM and SEM techniques. The feasibility of using CoFe2O4?SiO2-NH-βCD-BF3 as a magnetically recoverable catalyst was confirmed in the modified-Ritter reaction. The result showed that this novel nano-composite could serve as an efficient nanoreactor bearing super-acidic sites formed by immobilized BF3 and reuse at least for 6 times without loss in activity.
- Hamadi, Hosein,Zanjani, Zohreh,Yadollahi, Mahtab
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Read Online
- SO42-/CexZr1-xO2-catalyzed synthesis of N-tert-butylamides from various nitriles under solvent-free conditions
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The synthesis of N-tert-butylamides using SO4 2-/CexZr1-x O2 catalysts under solvent-free conditions is reported. The methodology has several advantages such as reusability of the catalyst, solvent-free conditions, easy workup, and comparable yield of N-tert-butylamides. A variety of aliphatic, aromatic, and acid-sensitive substrates give high to moderate yields of the corresponding N-tert-butylamides. Surface acidities of the catalysts were correlated with the results obtained. To the best of our knowledge, this is the first report of a modified Ritter reaction on SO42-/CexZr1-x O2 using tert-butyl acetate as carbocationic source.
- Kahandal, Sandeep S.,Kale, Sandip R.,Disale, Shamrao T.,Jayaram, Radha V.
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Read Online
- Application of SiO2-Pr-SO3H as an efficient catalyst in the Ritter reaction
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Sulfonic-acid-functionalized silica was applied as an efficient heterogeneous acid catalyst in the Ritter reaction to prepare amides by reaction of various benzylic, allylic, and tertiary alcohols with various nitriles in good to excellent yields under solvent-free conditions. The simplicity of the reaction, recovery of catalyst without loss of reactivity, high yield of products, and short reaction time represent improvements over many existing methods.
- Mohammadi Ziarani, Ghodsi,Badiei, Alireza,Dashtianeh, Zeinab,Gholamzadeh, Parisa,Mohtasham, Nina Hosseini
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Read Online
- Palladium-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted: O-carboranes containing α,β-unsaturated carbonyls
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With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The-COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.
- Li, Jiaoyi,Lu, Jian,Tian, Song,Wang, Qian,Zhang, Chuyi,Zhang, Jianwei,Zhou, Ling
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Read Online
- (P2O5/SiO2): a useful heterogeneous alternative for the Ritter reaction
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Tertiary alcohols as well as primary and secondary benzylic alcohols react efficiently with nitriles to give the corresponding amides in good to excellent yields in the presence of P2O5/SiO2 (60% w/w).
- Tamaddon, Fatemeh,Khoobi, Mehdi,Keshavarz, Elham
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Read Online
- Synthesis of N-isopropylacrylamide from acrylonitrile and isopropyl alcohol over H-ZSM-5
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A solid acid, H-ZSM-5 (Si/Al = 37), exhibited exceptionally high catalytic performance for synthesis of N-isopropylacrylamide from acrylonitrile and isopropyl alcohol in a solid-liquid reaction system at 423 K.
- Chen, Xin,Matsuda, Hideho,Okuhara, Toshio
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Read Online
- Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
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The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
- Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
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p. 319 - 330
(2021/10/29)
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- PROCESS FOR PREPARATION OF TERT-BUTYLAMINE AND PROPIONIC ACID SALTS FROM N-TERTIARY BUTYL ACRYLAMIDE
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Disclosed is a process (100) for conversion of N-tertiary butyl acrylamide to tert-butylamine and salts of propionic acid. The process comprises of first selectively reducing the vinylic double bond in N-tertiary butyl acrylamide by catalytic hydrogenation of an alcoholic solution of N-tertiary butyl acrylamide to provide N-tertiary buyl propanamide; recovering the hydrogenation catalyst by filtering the solution and treating the solution with an alkali to produce N-tertiary butylamine and corresponding alkali salt of propionic acid. The process converts of N-tertiary butyl acrylamide into value added products at milder reaction conditions, without producing any hazardous byproducts and effluents.
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Page/Page column 9; 10
(2021/11/13)
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- A convenient synthesis of N-tert-butyl amides by the reaction of di-tert-butyl dicarbonate and nitriles catalyzed by Cu(OTf)2
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The utility of Cu(OTf)2 as the catalyst for the synthesis of a series of N-tert-butyl amides in excellent isolated yields via the reaction of nitriles (alkyl, aryl, benzyl, and furyl nitriles) with di-tert-butyl dicarbonate is described. Cu(OTf)2 is a highly stable and efficient catalyst for the present Ritter reaction under solvent-free conditions at room temperature.
- Chen, Junqing,Feng, Chengliang,Ji, Min,Tang, Yuqi,Yang, Wanfeng
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p. 602 - 608
(2020/04/27)
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- MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0055; 0057; 0059
(2018/07/03)
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- A tertiary butyl acrylamide sulfonic acid production method
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The present invention relates to a tert-butyl acrylamide sulfonic acid production method, which comprises: 1) forming an acrylonitrile solution containing a sulfonating agent; 2) continuously introducing the solution into a horizontal stirring reactor to contact isobutene so as to form a slurry product; 3) filtering the slurry product to obtain the filter cake containing tert-butyl acrylamide sulfonic acid and the filtrate; 4) drying the filter cake obtained in the step 3) to obtain a tert-butyl acrylamide sulfonic acid crude product; 5) adopting an acetic acid aqueous solution to carry out recrystallization purification on the tert-butyl acrylamide sulfonic acid crude product obtained in the step 4) to obtain the tert-butyl acrylamide sulfonic acid with the mass content of more than 99.3% and the remaining waste liquid; and 6) evaporating the filtrate in the step 3) and/or the remaining waste liquid in the step 4) to obtain the waste residue, carrying out mixing contact on the waste residue and a treatment solvent, and carrying out solid-liquid separation to obtain the tert-butyl acrylamide sulfonic acid and the tert-butyl acrylamide.
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Paragraph 0042; 0043; 0044; 0050; 0051
(2016/12/01)
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- Mechanochemical ritter reaction: A rapid approach to functionalized amides at room temperature
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A fast and efficient mechanochemical Ritter reaction between alcohols and nitriles under mild conditions is demonstrated. The reaction proceeds rapidly at room temperature in a solvent-free or low-solvent environment by using a Br?nsted acid catalyst. Its general application has been verified through a substrate screening comprising a wide range of functionalized nitriles as well as secondary and tertiary alcohols. Gentle Ritter: A fast and efficient mechanochemical Ritter reaction under mild conditions is described. The reaction proceeds rapidly at room temperature in a solvent-free or low-solvent environment by using sulfuric acid as catalyst.
- Dokli, Irena,Gredi?ak, Matija
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supporting information
p. 2727 - 2732
(2015/04/27)
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- PURIFICATION METHOD OF N-tert-BUTYLACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a purification method performed under specific conditions which, when purifying N-tert-butylacrylamide (TBAM) by a sublimation method, can provide TBAM of high purity with little impurity contained in TBAM after purification and little coloration. SOLUTION: The purification method of TBAM comprises: separating from a reaction mixture 2-acrylamido-2-propanesulfonic acid obtained by reacting acrylonitrile, sulfuric acid, and isobutylene; recovering byproduct TBAM contained in the reaction mixture after the separation as crude crystals; and thereafter subliming the crude crystals from a molten liquid of 135 to 160°C under 600 Torr or less, and cooling the sublimation gas in stages in the order of 130 to 150°C at the outlet of a melting tank, 80 to 100°C at an upper part of a sublimation and collection tower, and 40 to 60°C at a lower part of the sublimation and collection tower. A content of the impurity, 3,3'-iminopropionitrile, in TBAM is 1000 ppm or less. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0039
(2020/10/10)
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- METHOD OF PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a method of producing N-substituted (meth)acrylamide of high purity under mild conditions. SOLUTION: This invention relates to a method of obtaining N-substituted (meth)acrylamide [3] by the detachment of an amine compound through the liquid-phase thermal decomposition of an aminopropionic acid amide derivative [1] in the presence of a catalyst mainly composed of silica, wherein R1-R5 are represented by H, a C1-32 alkyl group, and a hydroxyalkyl group. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0054; 0059; 0060
(2018/12/12)
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- Effective nitration of anilides and acrylamides by tert-butyl nitrite
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Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.
- Ji, Yi-Fei,Yan, Hong,Jiang, Qi-Bai
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p. 2051 - 2060
(2015/03/18)
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- Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides
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An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.
- Yaragorla, Srinivasarao,Singh, Garima,Lal Saini, Pyare,Reddy, M. Kesava
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p. 4657 - 4660
(2014/12/10)
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- KAl(SO4)2.12H2O as an eco-friendly and reusable catalyst for the synthesis of amides by the Ritter reaction
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KAl(SO4)2.12H2O (Alum) is an eco-friendly, inexpensive, readily available and reusable and was applied as catalyst to the synthesis of N-alkyl amides from nitriles and alcohols by the Ritter reaction. This solvent-free procedure is very simple with excellent yields and easy work-up.
- Sadeghi, Bahareh,Farahzadi, Ebrahim,Hassanabadi, Alireza
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p. 539 - 540
(2012/10/30)
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- THERMO-RESPONSIVE HYDROGEL COMPOSITIONS
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A thermo-responsive hydrogel, including a biocompatible monomer and/or polymer having an amino acid side chain. The hydrogel is thermo-responsive at a physiological temperature, and can include, incorporate, or encapsulate a treatment agent, such as a drug composition, a biomolecule, and/or a nanoparticle. The hydrogel is useful in delivering the treatment agent. The hydrogel is in a first physicochemical state for administration to a mammal. The hydrogel is thermo-responsive at a physiological temperature of the mammal, and changes to a second physicochemical state that is more solid than the first physicochemical state. In the second physicochemical state the thermo-responsive hydrogel releases the treatment agent.
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- Amberlyst-15 as a recyclable heterogeneous catalyst for synthesis of N-tert-butylamides via Ritter-type reaction
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Highly efficient method for the preparation of N-tert-butylamides by reaction of nitriles with tert-butylacetate is described using Amberlyst-15 as a recyclable heterogeneous catalyst. Selective amidation of benzonitrile in the presence of acetonitrile was also achieved.
- Mokhtary, Masoud,Goodarzi, Gholamreza
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experimental part
p. 293 - 296
(2012/05/07)
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- Polyvinylpolypyrrolidone-supported boron trifluoride; Highly efficient catalyst for the synthesis of N-tert-butyl amides
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Highly efficient method for the preparation of N-tert-butyl amides by reaction of nitriles with tert-butyl acetate is described using polyvinylpolypyrrolidone-supported boron trifluoride (PVPP-BF3) at 70 °C in good to excellent yields. Selective amidation of benzonitrile in the presence of acetonitrile was also achieved. polyvinylpolypyrrolidone-boron trifluoride complex shows non-corrosive and stable solid catalyst elevated Lewis acid property.
- Mokhtary, Masoud,Najafizadeh, Faranak
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experimental part
p. 576 - 582
(2012/06/30)
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- Ritter reactions in flow
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Flow me a Ritter: Ritter reactions are performed in a simple microreactor setup using tert-butylacetate as versatile carbocation source. The protocol avoids the handling of large amounts of hot concentrated sulfuric acid as low concentrations are optimal for rapid access tert-butyl- or diphenylmethyl- protected amides. Copyright
- Audiger, Logan,Watts, Kevin,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
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experimental part
p. 257 - 260
(2012/05/04)
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- Organocatalytic synthesis of amides from nitriles via the Ritter reaction
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A simple, inexpensive, environmentally friendly, and efficient route for the synthesis of a wide variety of amides in high yields via the Ritter reaction of alcohols with nitriles has been demonstrated. Pentafluorophenyl ammonium triflate (PFPAT) is used as an organocatalyst and is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.
- Khaksar, Samad,Fattahi, Eskandar,Fattahi, Esmail
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experimental part
p. 5943 - 5946
(2011/11/28)
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- Sulfated tungstate: An efficient catalyst for the Ritter reaction
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The use of sulfated tungstate as an efficient and reusable catalyst for the preparation of amides from alcohols and nitriles via the Ritter reaction pathway is discussed. The reaction proceeds under solvent free conditions. The Royal Society of Chemistry.
- Katkar, Kamlesh V.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
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supporting information; experimental part
p. 835 - 838
(2011/05/15)
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- One-pot synthesis of N-tert-butyl amides from alcohols, ethers and esters using ZnCl2/SiO2 as a recyclable heterogeneous catalyst
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ZnCl2/SiO2 has been found to be an efficient and reusable catalyst for conversion of alcohols, ethers and esters to corresponding amides via the Ritter reaction in high yield. It was found that benzonitrile reacted with tert-butyl acetate faster than the other sources of tert-butyl carbocation.
- Tamaddon, Fatemeh,Tavakoli, Fatemeh
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body text
p. 52 - 55
(2011/04/24)
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- Oil filter
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An oil filter includes a base, a cap mounted to the base to be detachable and forming a filter case in association with the base, a cylindrical filter element accommodated inside the filter case, and an inner cylinder disposed inside the filter element and attached to the cap. The cap has a head portion to which an engaging member is formed so as to extend inside the filter case, an axial one end of the inner cylinder is fitted to an outside of the engaging member to be detachable. The inner cylinder is provided with a stopper projecting in a radially outward direction thereof and having a tip end abutting against an inside surface of the filter case to thereby prevent the inner cylinder from falling down, and the stopper is disposed between the head portion of the cap and the filter element.
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- The Ritter reaction under incredibly green protocol: Nano magnetically silica-supported Br?nsted acid catalyst
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HClO4-functionalized silica-coated magnetic nanoparticles [γ-Fe2O3@SiO2-HClO4] (2.5 mol%) has been found to be a capable biocompatible and recyclable catalyst for highly efficient conversion of a variety of alcohols to corresponding amides via modified Ritter reaction in good to excellent yields. Since this heterogeneous catalyst can be simply removed by using an external magnetic device then recovered, it also enhances product purity and promises economic.
- Ma'mani, Leila,Heydari, Akbar,Sheykhan, Mehdi
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experimental part
p. 122 - 127
(2010/11/04)
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- Safe and efficient ritter reactions in flow
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Efficient mixing, temperature control and small environmental exposures allow reactions carried out in microfluidic de-vices to perform superior to their batch-type counterparts in conventional flasks. The Ritter reaction has been optimised for flow conditions leading to short reaction times and higher yields and also is more feasible with regards to safety, productivity and tolerance towards substrate functionalities.
- Brandt, Johan C.,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
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experimental part
p. 3099 - 3103
(2011/02/25)
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- An efficient and scalable ritter reaction for the synthesis of tert-butyl amides
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A scalable procedure for the conversion of nitriles to N-tert-butyl amides via the Ritter reaction was optimized employing tert-butyl acetate and acetic acid. The reaction has a broad scope for aromatic, alkyl, and α,β-unsaturated nitriles.
- Baum, Jean C.,Milne, Jacqueline E.,Murry, Jerry A.,Thiel, Oliver R.
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supporting information; experimental part
p. 2207 - 2209
(2009/07/01)
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- Exploring the scope of the 29G12 antibody catalyzed 1,3-dipolar cycloaddition reaction
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29G12 is a murine monoclonal antibody programmed to catalyze the regio- and enantioselective 1,3-dipolar cycloaddition reaction between 4-acetamidobenzonitrile N-oxide 1a and N,N-dimethylacrylamide 2a (Toker, J. D.; Wentworth, P., Jr.; Hu, Y.; Houk, K. N.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 3244). Given the unique nature of 29G12 as a protein biocatalyst for this chemical reaction, we have investigated both the substrate specificity and mechanistic parameters of the 29G12-catalyzed process. These studies have shown that while 29G12 is specific for its dipole substrate Ia, the antibody is highly promiscuous with respect to the dipolarophiles it can process. 29G12 accepts a bulky hydrophobic dipolarophile cosubstrate, with rates of product formation up to 70-fold faster than with the original substrate 2a. In all cases, the respective isoxazoline products are produced with exquisite regio- and stereochemical control (78-98% ee). Comparison between the steady-state kinetic parameters from the 29G12-catalyzed reaction of 1a with the most efficient versus the original dipolarophile cosubstrate (2m and 2a, respectively), reveals that while the effective molarities (EM)s are almost identical (EM (2m) 26 M; EM(2a) 23 M), the affinity of 29G12 for the larger dipolarophile 2m is more than 1 order of magnitude higher than for 2a [Km(2m) 0.44 ± 0.04 mM; Km(2a) 5.8 ± 0.4 mM]. Furthermore, when 2m is the cosubstrate, the affinity of 29G12 for its dipole 1a is also greatly improved [Km(1a) 0.82 ± 0.1 mM compared to Km(1a) 3.4 ± 0.4 mM when 2a is the cosubstrate]. An analysis of the temperature dependence of the 29G12-catalyzed reaction between 1a and 2m reveals that catalysis is achieved via a decrease in enthalpy of activation (ΔΔH? 4.4 kcal mol-1) and involves a large increase in the entropy of activation (ΔΔS? 10.4 eu). The improved affinity of 29G12 for the nitrile oxide Ia in the presence of 2m, coupled with the increase in ΔΔS? during the 29G12-catalyzed reaction between 1a and 2m supports the notion of a structural reorganization of the active site to facilitate this antibody-catalyzed reaction.
- Toker, Jonathan D.,Tremblay, Martin R.,Yli-Kauhaluoma, Jari,Wentworth, Anita D.,Zhou, Bin,Wentworth Jr., Paul,Janda, Kim D.
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p. 7810 - 7815
(2007/10/03)
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- Reactions on a Solid Surface. A Simple, Economical, and Efficient Acylation of Alcohols, Amines over Al2O3
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Al2O3 brings about a rapid acylation of a range of alcohols and amines with acid chlorides and acid anhydrides, respectively. Amines are easily Boc- and Cbz-protected on reaction with Boc-anhydride and Cbz-Cl, respectively. The acylation of phenols is slow enough to allow chemoselective acylation of alcohols and amines in the presence of phenols.
- Yadav, Veejendra K.,Babu, K. Ganesh
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p. 577 - 580
(2007/10/03)
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- Nucleophilic Addition to Electron-Rich Heteroaromatics: Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides
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(Matrix presented) Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.
- Clayden, Jonathan,Turnbull, Rachel,Pinto, Ivan
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p. 609 - 611
(2007/10/03)
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- Rare earth exchanged HY zeolite, an efficient catalyst for the synthesis of N-monosubstituted amides
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The use of rare earth exchanged HY (RE HY) zeolite catalyst for the synthesis of N-monosubstituted amides 3a-g starting from alcohols 1 and nitriles 2 in good yields is described
- Deshmukh, A. R. A. S.,Gumaste, V. K.,Bhawal, B. M.
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p. 369 - 371
(2007/10/03)
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- SYNTHESIS OF 2-ACRYLAMIDO-2-METHYLPROPANESULFONIC ACID - A NEW MONOMER FOR WATER-SOLUBLE POLYMERS
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The results are presented of synthesis of 2-acrylamido-2-methylpropanesulfonic acid from acrylonitrile and 2-methylpropene in the presence of oleum.The conditions for synthesis and isolation of the desired product have been optimized.The main product and by-products have been identified.
- Khalistova, I. D.,Podgornova, V. A.
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p. 1185 - 1188
(2007/10/02)
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- Reactions of Phenols with Thianthrene Cation Radical
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The phenols 2-R1-6-R2-phenol 1a-g in which R1 = R2 = tert-butyl, methyl, isopropyl, Cl, Br, F, and H reacted with thianthrene cation radical perchlorate (TH+ClO4-) to give 5-(4-hydroxyaryl)thianthreniumyl perchlorates 2a-g in good yield. o-Allylphenol (1i) behaved similarly. o-tert-Butylphenol (1h) gave both 5-(3-tert-butyl-4-hydroxyphenyl)thianthreniumyl perchlorate (2h) and a quinonoidal perchlorate (3), namely, 5-(3-thianthreniumyl-5-tert-butyl-6-oxo-2,4-cyclohexadien-1-ylidene)-5,5-dihydrothianthrene perchlorate.The 2,6-di-tert-butyl-4-R3-phenols 4a-c, R3 = tert-butyl, methoxy, and methyl, reacted with Th+ClO4- in nitrile solvents (RCN) to give 2-R-5-R3-7-tert-butylbenzoxazoles 5a-e.The tert-butyl group that was displaced by RCN in forming 5 was converted into t-BuNHCOR (8), tert-butyl alcohol, and isobutene.In contrast, 2-tert-butyl-4,6-dimethylphenol (9) gave, in CH3CN, 4-tert-butyl-2,5,7-trimethylbenzoxazole (11), that is, with migration of the displaced tert-butyl group.The reactions of 4-tert-butylphenol (14) and 2,4-di-tert-butylphenol (17) are also described.
- Shin, Seung-Rim,Shine, Henry J.
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p. 2706 - 2710
(2007/10/02)
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- N-substituted-3-iodopropiolamide, production and use thereof
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A novel amide compound, more particularly N-substituted-3-iodopropiolamide compound, which exhibits excellent antibacterial, antifungal, insecticidal, antialgal, miticidal and anti-termite activity; a method for producing the amide compound; and a noxious organisms controlling agent containing said amide compound.
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- Process for preparing isothiazolones
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The process involves the cofeeding of an acrylonitrile with an appropriate alcohol or its equivalent and a strong acid to form an acrylamide which is thiolated to form a mercapto-propionamide which is halogenated to afford the desired biocidally active isothiazolones. This invention relates to a novel process for preparing N-substituted 3-mercaptopropionamides, an intermediate in the preparation of isothiazolones.
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- Process for the preparation of N-alkyl-substituted carboxylic acid amides
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An improved process for the preparation of N-alkyl-substituted carboxylic acid amides by reaction of a component which forms a carbonium ion with a nitrile, the improvement residing in carrying out the process in the presence of an acid which is inert under distillation conditions and separating the reaction mixture by distillation.
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- N-monosubstituted amide production
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N-monosubstituted amides are prepared from nitriles and either olefinically unsaturated hydrocarbons or secondary or tertiary alcohols in the presence of a group VIII metal catalyst. The amides produced by the process of this invention are useful as solvents, organic synthesis intermediates, pesticides, cationic surface active agents, etc.
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