1934-92-5

Usage

Uses

Used in Pharmaceutical Industry:
N-methylbenzanilide is used as a key intermediate for the production of various pharmaceuticals, leveraging its ability to participate in a wide range of chemical reactions to facilitate the synthesis of medicinal compounds.
Used in Dye Industry:
In the dye industry, N-methylbenzanilide is utilized as an intermediate for the synthesis of different types of dyes, capitalizing on its chemical properties to create a variety of colorants for various applications.
Used in Organic Synthesis:
N-methylbenzanilide is employed as a reagent in organic synthesis, where its versatility allows for the creation of a broad spectrum of organic molecules, contributing to the development of new chemical entities and materials.

InChI:InChI=1/C14H13NO/c1-15(13-10-6-3-7-11-13)14(16)12-8-4-2-5-9-12/h2-11H,1H3

Upstream product

• 93-98-1 N-phenyl benzoyl amide 
• 6780-39-8 E-[2-methoxy-1-phenyl-methylene]-phenylamine 
• 98-88-4 benzoyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 100-61-8 N-methylaniline 
• 65-85-0 benzoic acid 
• 74-88-4 methyl iodide 
• 18106-71-3 dimethyl benzoylphosphonate 
• 88070-48-8 N-methylbenzamide 
• 83566-44-3 tetraphenylbismuth 4-methylbenzenesulfonate 
• 69859-25-2 3-chloro-N-methyl-N-phenylbenzothioamide 
• 2628-58-2 N-methylthiobenzanilide 
• 33224-04-3 N-methyl-N-phenyl-2-nitrobenzenesulfenanilide 
• 60036-62-6 ((E)-2-Methoxy-1,2-diphenyl-vinyl)-methyl-phenyl-amine 

Downstream Products

• 33672-82-1 N-(4-nitrophenyl)-N-methylbenzamide 
• 2628-58-2 N-methylthiobenzanilide 
• 56844-88-3 N'-benzyl-N-methyl-N-phenyl-benzamidine 
• 100-52-7 benzaldehyde 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 479-45-8 tetryl 
• 530-44-9 4-(Dimethylamino)benzophenone 
• 93-89-0 benzoic acid ethyl ester 
• 5496-57-1 N-methyl-N-(2-nitrophenyl)benzamide 
• 6941-23-7 1,2-bis(N-methyl-N-phenylamino)-1,2-diphenylethane 
• 91632-83-6 3-(N-methyl-N-phenylamino)-3-phenylpropannitril 
• 65-85-0 benzoic acid 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 74-87-3 methylene chloride 

Relevant academic research and scientific papers

Anomalous dual fluorescence of benzanilide

The absorption and fluorescence spectra of benzanilide and N-methylbenzanilide have been investigated in solution and low-temperature glasses and assigned with the aid of ZINDO calculations. The anomalous dual fluorescence observed by previous workers has been assigned to the two lowest singlet states of benzanilide. The lower energy n,π* state is populated by excitation in the long-wavelength tail of the absorption band. Its fluorescence is readily detected in low-temperature glasses and at room temperature in aromatic solvents. Large NMR solvent-induced shifts provide evidence for ground-state complex formation of benzanilide with aromatic solvents. The higher energy π,π* state is populated by excitation of an allowed transition. It undergoes twisting about the amide C-N bond to form a fluorescent twisted intramolecular charge-transfer state with a maximum of 520 nm in benzene solution. In rigid glasses twisting to form the twisted charge-transfer state cannot occur, and the π,π* state undergoes internal conversion to the lower energy n,π* state.

Simple and convenient synthesis of tertiary benzanilides using dichlorotriphenylphosphorane

Various tertiary benzanilide derivatives were effectively synthesized from substituted benzoic acid and N-monoalkylated aniline using dichlorotriphenylphosphorane in chloroform. Yields were generally high, even when an electron-withdrawing group substituted the aromatic ring of aniline, or when an electron-donating group substituted the aromatic ring of benzoic acid. Allyl, Boc, MPM and the Z group were unaffected under these conditions.

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N -Acylsaccharins

The use of tertiary amines as surrogates for secondary amines has prominent advantages in terms of stabilization and ease of handling. A Ni-catalyzed transamidation of N -acylsaccharins with tertiary aromatic amines is reported. By using tert -butyl hydroperoxide as the terminal oxidant, this reaction permits selective cleavage of the C(sp 3)-N bonds of unsymmetrical tertiary aromatic amines depending on the sizes of the alkyl substituents.

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

Preparation of alkylated compounds using the trialkylphosphate

[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in waterviabenzylic sp3C-H activation

A magnetite-reduced graphene oxide-supported CuO nanocomposite (rGO/Fe3O4-CuO) was preparedviaa facile chemical method and characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), UV-vis spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive spectroscopy (EDS), Brunauer-Emmett-Teller (BET) analysis, vibrating-sample magnetometry (VSM), and thermogravimetric (TG) analysis. The catalytic activity of the rGO/Fe3O4-CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals usingtert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation into a single operation. Moreover, the synthesized nanocomposites can be separated from the reaction mixtures using an external magnet and reused in six consecutive runs without a noticeable decrease in the catalytic activity.