2990-06-9

Basic information

• Product Name: N-(4-chlorophenyl)-2-phenylacetamide
• Synonyms: N-(4-chlorophenyl)-2-phenylacetamide;2-Phenyl-N-(4-chlorophenyl)acetamide;N-(4-Chlorophenyl)benzeneacetamide;BenzeneacetaMide, N-(4-chlorophenyl)-
• CAS NO: 2990-06-9
• Molecular Formula: C₁₄H₁₂ClNO
• Molecular Weight: 0
• Mol File: 2990-06-9.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-chlorophenyl)-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-chlorophenyl)-2-phenylacetamide(2990-06-9)
• EPA Substance Registry System: N-(4-chlorophenyl)-2-phenylacetamide(2990-06-9)

Safety Data

• Hazardous Substances Data: 2990-06-9(Hazardous Substances Data)

Upstream product

• 20265-96-7 p-chloroaniline hydrochloride 
• 140-29-4 phenylacetonitrile 
• 15485-22-0 4-chloro-N-[(4-methoxyphenyl)methylidene]aniline 
• 103-80-0 phenylacetyl chloride 
• 106-47-8 4-chloro-aniline 
• 103-81-1 Benzeneacetamide 
• 1011269-15-0 (4-chlorophenyl)-phenylethynyl-carbamic acid tert-butyl ester 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 201230-82-2 carbon monoxide 
• 27992-27-4 sodium 2-benzylidene-1-tosylhydrazin-1-ide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 103-83-3 N,N'-dimethylbenzylamine 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 

Downstream Products

• 32283-45-7 3-chloro-1-(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione 
• 28193-68-2 N-(4-chlorophenyl)-α-oxophenylacetamide 
• 59211-36-8 4-chloro-N-methyl-N-phenethylaniline 
• 1739-04-4 N-(4-chlorophenyl)-N-(2-phenylethyl)amine 

Relevant articles and documents

A simple and greener approach for the amide bond formation employing FeCl3 as a catalyst

Catalytic use of FeCl3 in the presence of glacial AcOH for the direct amidation of acid with amine in toluene has been described in this paper. The protocol worked well for the less nucleophilic aniline and its variants which gave the best results under the present reaction conditions. Amidation of bromoacetic acid and sterically hindered amino acid also proceed effectively to yield the corresponding amides. The protocol is catalytic and circumvents the use of stoichiometric amounts of reagents. The reaction led to water soluble by-products and thus makes the product isolation easier.

Synthesis of α-ketoamides using potassium superoxide (KO2) as an oxidizing agent

A simple and convenient method for the synthesis of α-ketoamides by the oxidation of aryl acetamides using potassium superoxide (KO2) as an oxidizing agent is disclosed here. The scope of the developed method is successfully tested with fifteen substrates. In addition, the utility of method has been demonstrated by synthesizing an orexin receptor antagonist, a medicinally interesting compound.

[Co(MeTAA)] Metalloradical Catalytic Route to Ketenes via Carbonylation of Carbene Radicals

An efficient synthetic strategy towards beta-lactams, amides, and esters involving “in situ” generation of ketenes and subsequent trapping with nucleophiles is presented. Carbonylation of carbene radical intermediates using the cheap and highly active cobalt(II) tetramethyltetraaza[14]annulene catalyst [Co(MeTAA)] provides a convenient one-pot synthetic protocol towards substituted ketenes. N-tosylhydrazones are used as carbene precursors, thereby bridging the gap between aldehydes and ketenes. Activation of these carbene precursors by the metalloradical cobalt(II) catalyst affords CoIII-carbene radicals, which subsequently react with carbon monoxide to form ketenes. In the presence of a nucleophile (imine, alcohol, or amine) in the reaction medium the ketene is immediately trapped, resulting in the desired products in a one-pot synthetic protocol. The β-lactams formed upon reaction with imines are produced in a highly trans-selective manner.