95725-09-0

Basic information

• Product Name: Benzeneacetamide, N-methyl-a-oxo-N-(phenylmethyl)-
• CAS NO: 95725-09-0
• Molecular Formula: C16H15NO2
• Molecular Weight: 253.301
• Mol File: 95725-09-0.mol

Chemical Properties

• CAS DataBase Reference: Benzeneacetamide, N-methyl-a-oxo-N-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetamide, N-methyl-a-oxo-N-(phenylmethyl)-(95725-09-0)
• EPA Substance Registry System: Benzeneacetamide, N-methyl-a-oxo-N-(phenylmethyl)-(95725-09-0)

Safety Data

• Hazardous Substances Data: 95725-09-0(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 
• 103-67-3 benzyl-methyl-amine 
• 591-50-4 iodobenzene 
• 13665-04-8 2,2-dibromoacetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 98-86-2 acetophenone 
• 100-61-8 N-methylaniline 
• 721-04-0 2-phenoxy-1-phenylethanone 
• 98-85-1 1-Phenylethanol 
• 611-73-4 Benzoylformic acid 
• 93-56-1 phenylethane 1,2-diol 

Relevant articles and documents

CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides

Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).

Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides

A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100?000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism.

Cu(i)-Functionalized SBA-16: An efficient catalyst for the synthesis of α-ketoamides under moderate conditions

An efficient catalyst based on the cage-like mesoporous material SBA-16 as the support and Cu(i) as active sites has been successfully prepared. The catalyst demonstrated high catalytic activity (up to 88%) in the direct oxidative synthesis of α-ketoamides between acetophenone and piperidine, employing O2 from open air as the oxidant without other additives. A heterogeneous catalyst was applied in this reaction for the first time, and the catalyst could be easily separated from the reaction system by filtration and reused several times without a significant loss of activity.

Copper-catalyzed one-pot synthesis of α-ketoamides from 1-arylethanols

A copper-catalyzed one-pot strategy for the synthesis of α-ketoamides from 1-arylethanols is described. This triple oxidation of 1-arylethanols involves alcohol oxidation, sp3 C-H oxidation, and oxidative amidation with amines. The protocol is highly efficient, delivering α-ketoamides in good to excellent yields.

Mesoporous poly-melamine-formaldehyde stabilized palladium nanoparticle (Pd@mPMF) catalyzed mono and double carbonylation of aryl halides with amines

A new mesoporous poly-melamine-formaldehyde material supported Pd nano catalyst (mPMF-Pd0) has been synthesized and characterized by thermogravimetric analysis (TGA), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectrometry (EDS), high-resolution transmission electron microscopy (HRTEM), UV-vis diffuse reflection spectroscopy (DRS), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS) and a N2 adsorption study. The mPMF-Pd0 material showed very good catalytic activity in the field of mono and double amino carbonylation of aryl bromides/iodides. Moreover, the catalyst is easily recoverable and can be reused six times without appreciable loss of catalytic activity in the above reactions. So, the highly dispersed and strongly bound palladium(0) sites in the mPMF-Pd0 could be responsible for the observed high activities. Due to strong binding with the functional groups of the polymer, no evidence of leached Pd from the catalyst during the course of reaction occurred, suggesting true heterogeneity in the catalytic process. This journal is

Chemical conversion of β-O-4 lignin linkage models through Cu-catalyzed aerobic amide bond formation

Methods for conversion of the lignin β-O-4 models into amide derivatives and phenols have been developed, which is achieved via chemo-selective oxidation of the secondary benzylic alcohol and subsequent Cu-catalyzed aerobic amide bond formation.

Coupling of methyl ketones and primary or secondary amines leading to α-ketoamides

A metal-free oxidative coupling of methyl ketones and primary or secondary amines to α-ketoamides has been developed. Four intermediates, α-iodoketone, α-aminoketone, iminium intermediate, and α-hydroxy amine have been identified through a series of control experiments. The atom-economic methodology can be scaled-up, tolerates a variety of functional groups, and is operationally simple.

Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

A facile and expeditious synthetic approach for the synthesis of α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2.

Copper-catalyzed aerobic oxidative synthesis of α-ketoamides from methyl ketones, amines and NIS at room temperature

A simple, efficient and practical copper-catalyzed aerobic oxidative synthesis of α-ketoamides from aryl methyl ketones, aliphatic amines and N-iodosuccinimide (NIS) has been developed. The one-pot reaction may proceed smoothly at room temperature in the open air. The possible mechanism for the formation of α-ketoamides was proposed. Molecular oxygen in air functions as both an oxidant and an oxygen source.