5465-00-9

Usage

Uses

Used in Pharmaceutical Industry:
N-ethyl-2-phenyl-acetamide is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to form amide bonds with other molecules makes it a valuable component in the development of new drugs and medications.
Used in Chemical Research:
In the field of chemical research, N-ethyl-2-phenyl-acetamide serves as a model compound for studying the properties and reactivity of amides. It can be used to investigate the mechanisms of amide formation and hydrolysis, as well as to explore the effects of different substituents on the reactivity and stability of the amide bond.
Used in Material Science:
N-ethyl-2-phenyl-acetamide may also find applications in material science, particularly in the development of new polymers and materials with specific properties. Its ability to form strong intermolecular interactions could be exploited to create materials with enhanced mechanical strength, thermal stability, or other desirable characteristics.

Synthesis Reference(s)

Synthesis, p. 181, 1984 DOI: 10.1055/s-1984-30772

InChI:InChI=1/C10H13NO/c1-2-11-10(12)8-9-6-4-3-5-7-9/h3-7H,2,8H2,1H3,(H,11,12)

Upstream product

• 140-29-4 phenylacetonitrile 
• 4283-15-2 phenylacetylcarbamic acid ethyl ester 
• 75-04-7 ethylamine 
• 74-96-4 ethyl bromide 
• 103-81-1 Benzeneacetamide 
• 64-17-5 ethanol 
• 60-12-8 2-phenylethanol 
• 75-05-8 acetonitrile 
• 103-82-2 phenylacetic acid 
• 100-51-6 benzyl alcohol 
• 103-80-0 phenylacetyl chloride 
• 17674-16-7 benzyl triflate 
• 693-29-8 N,N'-diethylcarbodiimide 
• 100-44-7 benzyl chloride 

Downstream Products

• 22002-68-2 N-ethyl-2-phenylethanamine 
• 2431-96-1 N,N-diethylphenylacetamide 
• 50613-04-2 N-Ethyl-2-phenyl-acetimidic acid methyl ester 

Relevant academic research and scientific papers

Solvent-Free N-Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica–Alumina

The N-alkylation of phenylacetamide with benzyl alcohol has been studied using Ni/SiO2–Al2O3. In the optimized conditions, the desired product was isolated in an excellent 98 % yield. The reaction could advantageously be performed in neat conditions, with a slight excess of amide and a catalytic amount of base. These conditions were tested on a large range of amides and alcohols, affording 24 compounds in 13 to 99 % isolated yields.

Nickel-Catalyzed Reductive Addition of Aryl/Benzyl Halides and Pseudohalides to Carbodiimides for the Synthesis of Amides

A Nickel-catalyzed reductive process is described for the direct amidation of benzyl and aryl halides using carbodiimides as the amidating agent. Moreover, aryl and benzyl C–O electrophiles such as triflate, acetate, tosylate, trityl ether, and pivalate were converted into amides using this method. The in-situ-generated Ni0acts as a catalyst for the reaction at room temperature for benzylic substrates, and 70 °C for aryl electrophiles. This new nickel-catalyzed reductive coupling protocol provides a general and operationally simple method for the synthesis of diverse amides using carbodiimides. Amides bearing bulky substituents can be synthesized by this strategy in high yield, which demonstrates its effectiveness in amide synthesis.

One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents

A method is reported for the one-carbon homologation of an alcohol to the extended carboxylic acid, ester, or amide. The process involves the Mitsunobu reaction with an alkoxymalononitrile, followed by unmasking in the presence of a suitable nucleophile. The homologation and unmasking can even be performed in a one-pot process in high yield.

Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation

2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.

Carboxyl activation of 3-mercapto-5,6-diphenyl-1,2,4-triazine through N-phenylacetyl-5,6-diphenyl-1,2,4-triazine-3-thione

The carboxyl activation ability of 3-mercapto-5,6-diphenyl-1,2,4-triazine has been established by coverting it into N-phenylacetyl-5,6-diphenyl-1,2,4-triazine-3-thione and this was then subjected to aminolysis and esterification with amines and alcohols respectively and selective aminolysis with aminoalcohols-monitoring chemically and confirmed spectrophotometrically by UV-Visible scannings. It could be proved that 3- mercapto-5,6-diphenyl-1,2,4-triazine is an efficient carboxyl activating group which can be successfully applied in solid phase peptide synthesis.

Ruthenium-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy

A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrile is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the α-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single byproduct. A utility of the reaction was demonstrated by synthesizing 13C or 15N isotope-labeled amides without involvement of any separate reduction and oxidation step.

An efficient protocol for the preparation of amides by copper-catalyzed reactions between nitriles and amines in water

The reactions between nitriles and amines catalyzed by Cu(OAc)2 and 2-piperidinecarboxylic acid were carried out in pure water without any other additives. A variety of substituted amides can be obtained in moderate to good yields up to 90%.

Oxidative C-H homodimerization of phenylacetamides

A range of secondary and tertiary phenylacetamides undergo oxidative homodimerization to afford biaryls. The reaction proceeds under palladium catalysis in the presence of a copper cocatalyst and oxygen and is most effective for electron-rich substrates.

Helper inducers for differentiation therapy and chemoprevention of cancer

Cancer cells are blocked from entering differentiation pathways because of abnormal methylation enzymes, which are responsible for keeping cancer cells in cycling state. Effective differentiation inducers are those capable of acting directly or indirectly to convert abnormal methylation enzymes into normal enzymes, thereby enabling cancer cells to undergo terminal differentiation. Differentiation employing inducer alone often can not reach completion because of the damage created by the inducer. Such damage can be prevented if differentiation is induced in the presence of helper inducers, which are basically inhibitors of the component enzymes of methylation. Thus, differentiation induced in the presence of helper inducers is more likely to reach completion. Therefore, helper inducers are essential components of differentiation therapy, not just merely to potentiate the activity of differentiation inducers. The present inventors discover that alkyl phenylacetamides, alkyl phenylacetate, 2,4-dichlorophenylacetate, and indole acetate are potent helper inducers.

The Selective N-Monoalkylation of Amides with Alkyl Halides in the Presence of Alumina and KOH

The effects of alumina impregnated with KOH (KOH/Al2O3) and a mixture of alumina and powdered KOH (KOH+Al2O3) have been examined using the alkylation of benzamide under various conditions.In each case, alkylation occurs exclusively in the pores of the alumina, the extent depending upon the alumina-pore size.For both yield and selectivity for N-monoalkylation, KOH+Al2O3 is superior to KOH/Al2O3.Dioxane is the best of the solvents employed.It is proposed that, in dioxane, an enolate-like species, PhC(O-K+)=NR', exists as stable ion pair aggregates, which are true reactants in the pore.This method, using KOH/Al2O3 or KOH+Al2O3, has been applied to N-alkylation of the other amides, giving the N-monoalkylated products in substantial yields with extremely high selectivities. 2-Phenylacetamide is regioselectively N-monoalkylated in high yields.This regioselectivity is explained in terms of steric hindrance.