762-84-5Relevant articles and documents
FTIR spectroscopic study of hydrogen bonding and solvent induced frequency shifts of N-tert-butylacetamide
Jovi?, Branislav,Nikoli?, Aleksandar,Petrovi?
, p. 140 - 143 (2013)
This paper reports the results of FTIR study of N-tert-butylacetamide in carbon tetrachloride solution and in presence of seven different molecules as H acceptors. The spectroscopic characteristics for NH?O hydrogen bonded complexes are given. Also, the equilibrium constants for 1:1 complex formation, at 25 °C were determined by using IR measurements. Frequency shifts of carbonyl stretching vibration ν(CO) of N-tert-butylacetamide in the same organic H acceptors was also investigated. The wavenumbers of carbonyl stretching vibration ν(CO) were correlated with the solvent acceptor number (AN) and the linear solvation energy relationships (LSERs).
Surface ligands enhance the catalytic activity of supported Au nanoparticles for the aerobic α-oxidation of amines to amides
Chatterjee, Puranjan,Kanbur, Uddhav,Manzano, J. Sebastián,Sadow, Aaron D.,Slowing, Igor I.,Wang, Hsin
, p. 1922 - 1933 (2022/04/07)
The catalytic aerobic α-oxidation of amines in water is an atom economic and green alternative to current methods of amide synthesis. The reaction uses O2 as terminal oxidant, avoids hazardous reactants and gives water as the only byproduct. Here we report that the catalytic activity of silica-supported Au nanoparticles for the aerobic α-oxidation of amines can be improved by tethering pyridyl ligands to the support. In contrast, immobilization of thiol groups on the material gives activities comparable to Au supported on bare silica. Our studies indicate that the ligands affect the electronic properties of the Au nanoparticles and thereby determine their ability to activate O2 and mediate C-H cleavage in the amine substrate. The reaction likely proceeds via an Au catalyzed β-hydride elimination enabled by backdonation from electron-rich metal to the orbital. O2, which is also activated on electron-rich Au, acts as a scavenger to remove H from the metal surface and regenerate the active sites. The mechanistic understanding of the catalytic conversion led to a new approach for forming C-C bonds α to the N atoms of amines.
A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
supporting information, p. 1955 - 1958 (2021/03/02)
Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
Preparation method of acetamide compound
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Paragraph 0035-0047, (2021/05/19)
The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.
CoFe2O4?SiO2-NH-βCD-BF3 as a supramolecular nanocomposite: Synthesis, characterization and catalytic activity
Hamadi, Hosein,Zanjani, Zohreh,Yadollahi, Mahtab
, (2019/11/14)
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.
Chemoselective formation of C–N bond in wet acetonitrile using amberlyst-15(H) as a recyclable catalyst
Nandy, Sneha,Das, Asit Kumar,Bhar, Sanjay
supporting information, p. 3326 - 3336 (2020/08/13)
An economically efficient and environmentally benign protocol for the chemoselective one-pot synthesis of diversely N-substituted amides has been developed in good yield through the reaction of benzylic secondary alcohols as well as aliphatic tertiary alcohols and alkyl/aryl nitriles. Commercially available Amberlyst-15(H) has been utilized at 80 °C as an air-stable and reusable heterogeneous inexpensive solid acid catalyst without any anhydrous and inert environment. The attractive features of the present synthetic protocol are mild reaction conditions, short reaction time, excellent chemoselectivity, high atom economy and tolerance of various sensitive moieties.
New half-sandwich (η6-p-cymene)ruthenium(II) complexes with benzothiazole hydrazone Schiff base ligand: Synthesis, structural characterization and catalysis in transamidation of carboxamide with primary amines
Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy
supporting information, (2020/10/18)
Few half-sandwich (η6-p-cymene) ruthenium(II) complexes supported by benzothiazole hydrazone Schiff bases were synthesized. The new complexes possess the general formulae [Ru(η6-p-cymene)(L)Cl] (1-3) (L = salicyl((2-(benzothiazol-2-yl)hydrazono)methylphenol) (SAL-HBT), 2-((2-(benzothiazol-2-yl)hydrazono)methyl)-6 methoxyphenol) (VAN-HBT) or naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methyl phenol) (NAP-HBT). All compounds were fully studied by analytical, spectroscopic techniques (IR, NMR) and also by mass spectrometry. The solid state structure of the complex 3 reveals the coordination of p-cymene moieties with ruthenium(II) in a three-legged piano-stool geometry along with benzothiazole hydrazone Schiff base ligand in a monobasic bidentate fashion. The catalytic properties of the complexes were screened in transamidation of primary amide with amines after optimization with respect to solvent, substituents, time and catalyst loading. The results show that the complex 3 is the most efficient catalyst for the transamidation of carboxamides with amines.
Silicon-Mediated Coupling of Carbon Monoxide, Ammonia, and Primary Amines to Form Acetamides
Luecke, Marcel-Philip,Kostenko, Arseni,Wang, Yuwen,Yao, Shenglai,Driess, Matthias
supporting information, p. 12940 - 12944 (2019/07/18)
For the first time, a direct transformation of CO, NH3, and primary amines into acetamides, mediated by a main-group element (silicon), is reported. Starting point is the selective deoxygenative reductive homocoupling of two CO molecules by the Fc-bis(silylene) 1 a (Fc=ferrocendiyl) as a reducing agent, which forms the ferrocendiyl-bridged disila(μ-O)(μ-CCO)ketene intermediate 2 a. Exposing 2 a to NH3 (1 bar, 298 K) and benzylamine yields the Fc-disiloxanediamines [Fc(RHNSi-O-SiNHR)] 5 a (R=H) and 5 b (R=benzyl) under release of the respective acetamides H3CC(O)NHR, as confirmed by 13C-isotope-labelling experiments. IR and NMR studies of the reaction reveal a four-step mechanism involving an N-silylated carboxamide that can be isolated and fully characterized. The striking reaction mechanism for this unprecedented transformation involves a facile Si?C bond cleavage and ammonolysis of a Si?O bond, and has been demonstrated experimentally and by quantum-chemical calculations.
Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
, p. 3532 - 3538 (2018/08/01)
Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
Sulfated choline ionic liquid-catalyzed acetamide synthesis by grindstone method
Kalla, Reddi Mohan Naidu,Lim, Jaehwa,Bae, Jaeyeong,Kim, Il
supporting information, p. 1595 - 1599 (2017/04/03)
Sulfated choline ionic liquid (SCIL) has been found to be an efficient solid acid IL catalyst for the protection of amine groups with acetic anhydride under solvent-free grindstone conditions. The attractive features of this new catalytic methodology include its sustainability, facile work-up procedure, economic viability, and biodegradability. The SCIL catalyst was characterized using infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The catalyst could be reused six times without significant loss in activity. Furthermore, no chromatographic separations were needed to obtain the desired products.
