5292-72-8

Upstream product

• 109-89-7 diethylamine 
• 25026-34-0 4-chlorophenacetyl chloride 
• 106-39-8 bromochlorobenzene 
• 685-91-6 diethylacetamide 
• 1878-66-6 4-chlorophenylacetic Acid 
• 58784-40-0 4-chlorophenyl isocyanate 
• 1497283-43-8 C₁₂H₁₆ClNO 

Downstream Products

• 1610734-25-2 2-(4-(tert-butyl)phenyl)-2-(4-chlorophenyl)-N,N-diethylacetamide 
• 1598387-25-7 2-(4-chlorophenyl)-N,N-diethyl-3,3-difluoro-3-(trimethylsilyl)propanamide 
• 1875-88-3 2-(4-Chlorophenyl)ethanol 
• 137958-84-0 2-(4-chlorophenyl)-N,N-diethylacrylamide 

Relevant academic research and scientific papers

Preparation method of aryl acetamide compound

The invention discloses a preparation method of an aryl acetamide compound. The method comprises the following steps: adding a palladium catalyst, a ligand, benzyl formate, tertiary amine and trifluoroacetic anhydride into an organic solvent, performing reacting at 130 DEG C for 24 hours, and after the reaction is completed, carrying out after-treatment to obtain the aryl acetamide compound. The preparation method is easy to operate, the after-treatment is simple and convenient, reaction initial raw materials are cheap and easily available, benzyl formate is taken as both a carbon monoxide source and a reactant, tertiary amine is taken as an amine source, substrate designability is high, substrate functional group tolerance range is wide, and reaction efficiency is high. What is noteworthyis that C-N bonds of the tertiary amine are broken in the reaction, no extra oxidizing agent is needed, various aryl acetamide compounds can be synthesized according to actual needs, and practicability is high.

P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions

A variant of P450 from Bacillus megaterium five mutations away from wild type is a highly active catalyst for cyclopropanation of a variety of acrylamide and acrylate olefins with ethyl diazoacetate (EDA). The very high rate of reaction enabled by histidine ligation allowed the reaction to be conducted under aerobic conditions. The promiscuity of this catalyst for a variety of substrates containing amides has enabled synthesis of a small library of precursors to levomilnacipran derivatives. This journal is

A general and practical palladium-catalyzed direct a-arylation of amides with aryl halides

An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indolebased phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pK a up to 35) were reversibly depotonated by lithium tert-butoxide (LiO-t-Bu), sodium tert-butoxide (NaO-t-Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe3)2].

Amination of phenylketenes. Substituent effect on amine-catalyzed tautomerization of amide enol

The transient intermediates with infrared bands at 1676-1680 cm -1 observed for reaction of substituted phenylketenes with diethylamine in acetonitrile were suggested to be the amide enols rather than the zwitterions on the basis of the theoretical calculations. A single broad band at 1674 cm-1 observed for reaction with the primary amines was attributed to overlap of two bands of the intermediate (amide enol) and the final product (amide). The substituent effect for the second-order rate constants of diethylamine-catalyzed tautomerization of the amide enol intermediates to give the amides was analyzed successfully by the Yukawa-Tsuno equation, giving a ρ value of 0.63 and an r- value of 1.31. The r- value larger than unity for pKa of phenols indicates that the negative charge formed at an oxygen atom of the amide enol at the transition state is significantly delocalized into the aromatic π-system through the ethenyl group. This r- value was considered to reflect an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ value attributes to the cyclic transition structure where the negative charge disperses in a six-member ring. Copyright 2013 John Wiley & Sons, Ltd. The substituent effect for the reaction of the amide enol intermediate generated from phenylketene with diethylamine has been analyzed. The large r- of 1.31 was attributed to an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ of 0.63 suggested the cyclic transition structure. Copyright

Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions

The intermolecular α-arylation and vinylation of amides by palladium-catalyzed coupling of aryl bromides and vinyl bromides with zinc enolates of amides is reported. Reactions of three different types of zinc enolates have been developed. The reactions of

On the Synthesis and Basicity of 1,3-Diaminoisoquinolines

A series of 6- and 7-substituted derivatives of 1,3-diaminoisoquinoline were synthesized by the reaction of N,N-diethylarylacetamides with POCl 3 and then with N,N-dimethylcyanamide. The products were identified by means of spectroscopic methods and their pKa dissociation constants were determined.