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 
• 100-61-8 N-methylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 65-85-0 benzoic acid 
• 74-88-4 methyl iodide 
• 74-96-4 ethyl bromide 
• 2628-58-2 N-methylthiobenzanilide 
• 88070-48-8 N-methylbenzamide 
• 83566-44-3 tetraphenylbismuth 4-methylbenzenesulfonate 
• 33224-04-3 N-methyl-N-phenyl-2-nitrobenzenesulfenanilide 
• 121884-88-6 C₁₅H₁₆NO₄P 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 530-44-9 4-(Dimethylamino)benzophenone 
• 93-89-0 benzoic acid ethyl ester 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 6941-23-7 1,2-bis(N-methyl-N-phenylamino)-1,2-diphenylethane 
• 91632-83-6 3-(N-methyl-N-phenylamino)-3-phenylpropannitril 
• 100-52-7 benzaldehyde 
• 72046-54-9 O,N-dimethyl-N-phenylbenzimidatonium trifluoromethanesulfonate 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 74-87-3 methylene chloride 
• 479-45-8 tetryl 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 100-51-6 benzyl alcohol 
• 100-61-8 N-methylaniline 
• 1557178-23-0 2-cyano-N-methyl-N-phenylbenzamide 

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.

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%.

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

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

Copper-catalyzed Goldberg-type C-N coupling in deep eutectic solvents (DESs) and water under aerobic conditions

An efficient and selectiveN-functionalization of amides is first reportedviaa CuI-catalyzed Goldberg-type C-N coupling reaction between aryl iodides and primary/secondary amides run either in Deep Eutectic Solvents (DESs) or water as sustainable reaction media, under mild and bench-type reaction conditions (absence of protecting atmosphere). Higher activities were observed in an aqueous medium, though the employment of DESs expanded and improved the scope of the reaction to include also aliphatic amides. Additional valuable features of the reported protocol include: (i) the possibility to scale up the reaction without any erosion of the yield/reaction time; (ii) the recyclability of both the catalyst and the eutectic solvent up to 4 consecutive runs; and (iii) the feasibility of the proposed catalytic system for the synthesis of biologically active molecules.

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.