5436-83-9

Usage

Uses

Used in Organic Synthesis:
N-benzyl-4-methyl-benzamide is used as a key intermediate for the synthesis of various organic compounds. Its amide group and aromatic structure make it a versatile building block in the creation of complex organic molecules.
Used in Pharmaceuticals:
In the pharmaceutical industry, N-benzyl-4-methyl-benzamide is utilized as a starting material or intermediate in the development of new drugs. Its unique chemical properties allow it to be modified and functionalized to create potential therapeutic agents.
Used in Agrochemicals:
N-benzyl-4-methyl-benzamide is also employed in the agrochemical sector as a raw material for the production of various pesticides and other agricultural chemicals. Its chemical structure can be tailored to target specific pests or enhance the effectiveness of existing products.
Used in Dyestuff:
In the dyestuff industry, N-benzyl-4-methyl-benzamide is used as a precursor for the synthesis of various dyes and pigments. Its aromatic nature and amide functionality contribute to the color properties and stability of the resulting dyes.

InChI:InChI=1/C15H15NO/c1-12-7-9-14(10-8-12)15(17)16-11-13-5-3-2-4-6-13/h2-10H,11H2,1H3,(H,16,17)

Upstream product

• 26218-73-5 3,4-bis(4-methylphenyl)-1,2,5-oxadiazole-N-oxide 
• 100-46-9 benzylamine 
• 24431-15-0 (E)-N-benzyl-1-(p-tolyl)methanimine 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-87-0 4-methyl-benzaldehyde 
• 1380086-03-2 C₁₁H₁₆O₂ 
• 106-38-7 para-bromotoluene 
• 36930-95-7 2,2,2-trichloro-1-(4-methylphenyl)ethanone 
• 29237-95-4 chloro-benzyl amine 
• 874-60-2 4-methyl-benzoyl chloride 
• 1644630-66-9 C₁₄H₁₀ClNO₄ 
• 108-88-3 toluene 
• 619-55-6 para-methylbenzamide 
• 104-85-8 para-methylbenzonitrile 

Downstream Products

• 24431-15-0 N-benzyl-p-tolylmethanimine 
• 68055-34-5 4-methylthiobenzoic acid benzylamide 
• 51891-99-7 3,4-dihydro-3-(4-methylphenyl)-2H-benz[e]-1,3-oxazine 
• 58010-65-4 N-(4-methylbenzoyl)benzamide 
• 10254-13-4 N-(Diphenylmethylen)-p-toloylsaeureamid 
• 891414-34-9 N,N-dibenzyl-N-(4-methylbenzyl)amine 
• 620-40-6 tribenzylamine 
• 55096-86-1 benzyl(4-methylbenzyl)amine 
• 103-49-1 dibenzylamine 
• 1430730-38-3 4-benzyl-5-(4-methylphenyl)-3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole 
• 1269762-43-7 C₇₅H₁₃NO 
• 5467-99-2 4-methylbenzoic acid benzyl ester 
• 1303614-34-7 C₁₅H₁₄N₂O₂ 
• 104-85-8 para-methylbenzonitrile 

Relevant academic research and scientific papers

Buchwald-Hartwig amination of aryl esters and chlorides catalyzed by the dianisole-decorated Pd-NHC complex

A modular and generic method for the Buchwald-Hartwig amination reactions of relatively unreactive aryl esters as acyl electrophiles and aryl chlorides as aryl electrophiles has been developed, leading to the efficient synthesis of amides/amines under air conditions and with low catalyst loadings. The success of this catalytic protocol is mainly attributed to the modification of the Pd-IPr skeleton with sterically hindered and electron-donating anisole groups. This method also features good functional group tolerance and excellent chemoselectivities. In summary, the results presented herein suggest the possibility of developing a versatile and general protocol for diverse electrophiles to undergo the Buchwald-Hartwig amination reactions, avoiding too much consideration of the reaction conditions for the substrate-dependent C-N bond formations.

TBAI-catalyzed C–N bond formation through oxidative coupling of benzyl bromides with amines: a new avenue to the synthesis of amides

A new green approach for the synthesis of amide through TBAI-catalyzed oxidative coupling of benzyl bromides with amine was developed in the presence of tert-butyl hydroperoxide (TBHP) as an oxidant. Various electron-donating and withdrawing groups containing benzyl bromides and various amines, were subjected to the reaction and transformed to the corresponding amide in good to excellent yields.

Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines

A one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible, and abundant reagents.

Alkali-modified heterogeneous Pd-catalyzed synthesis of acids, amides and esters from aryl halides using formic acid as the CO precursor

To establish an environmentally friendly green chemical process, we minimized and resolved a significant proportion of waste and hazards associated with conventional organic acids and molecular gases, such as carbon monoxide (CO). Herein, we report a facile and milder reaction procedure, using low temperatures/pressures and shorter reaction time for the carboxyl- and carbonylation of diverse arrays of aryl halides over a newly developed cationic Lewis-acid promoted Pd/Co3O4catalyst. Furthermore, the reaction proceeded in the absence of acid co-catalysts, and anhydrides for CO release. Catalyst reusability was achievedviascalable, safer, and practical reactions that provided moderate to high yields, paving the way for developing a novel environmentally benign method for synthesizing carboxylic acids, amides, and esters.

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Reductive N-alkylation of primary amides using nickel-nanoparticles

Here we report Ni-nanoparticles as reusable catalysts for reductive N-alkylation of amides. These Ni-nanoparticles based catalysts have been prepared by the template synthesis of tartaric acid and 2-methyl imidazole ligated Ni-complex on SiO2 and subsequent pyrolysis under argon. Applying optimal Ni-nanostructured catalyst, N-alkylation of aromatic and heterocyclic primary amides with different aldehydes in presence of molecular hydrogen was performed to access structurally diverse N-alkylated amides in good to excellent yields. In addition, the applicability of this N-alkylation protocol has been demonstrated for the selective functionalization of primary amide group in Levetiracetam drug.

N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation

A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is

Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands

The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.