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Usage

Uses

Used in Organic Synthesis:
N-Methyl-N-phenylbutanamide is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows it to be a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The presence of the phenyl group and the amide functionality make it a valuable intermediate in the development of complex molecular structures.
Used in Pharmaceutical Industry:
N-Methyl-N-phenylbutanamide is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its ability to form a wide range of derivatives makes it a valuable asset in the development of new drugs with specific therapeutic properties. N-Methyl-N-phenylbutanamide's reactivity and structural diversity enable chemists to design and synthesize novel drug candidates with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, N-Methyl-N-phenylbutanamide is used as a starting material for the development of new pesticides, herbicides, and other crop protection agents. Its chemical properties allow for the creation of compounds with targeted biological activity, which can help improve the efficiency and selectivity of these products in agricultural applications.
Used in Dye and Pigment Industry:
N-Methyl-N-phenylbutanamide is also used as a precursor in the synthesis of dyes and pigments. Its light brown color and chemical structure make it a suitable candidate for the development of new colorants with specific properties, such as improved lightfastness, stability, and solubility.
Used in Material Science:
In the field of material science, N-Methyl-N-phenylbutanamide can be used as a component in the development of advanced materials with specific properties. Its amide functionality and phenyl group can be exploited to create materials with tailored characteristics, such as improved mechanical strength, thermal stability, or electrical conductivity.

InChI:InChI=1/C11H15NO/c1-3-7-11(13)12(2)10-8-5-4-6-9-10/h4-6,8-9H,3,7H2,1-2H3

Upstream product

• 106-31-0 butanoic acid anhydride 
• 98-04-4 phenyltrimethylammonium iodide 
• 141-75-3 butyryl chloride 
• 100-61-8 N-methylaniline 
• 81712-01-8 Butyric acid (E)-2-(4-nitro-benzenesulfonyl)-vinyl ester 
• 93699-29-7 (Z)-2-(N-Methylanilino)-2-pentennitril 
• 57361-03-2 (E/Z)-2-(N-Methylanilino)-2-pentennitril 
• 120568-27-6 (E)-2-(Methyl-phenyl-amino)-pent-3-enenitrile 
• 105-54-4 butanoic acid ethyl ester 
• 123-72-8 butyraldehyde 
• 121-69-7 N,N-dimethyl-aniline 
• 99-97-8 Dimethyl-p-toluidine 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 1197-19-9 4-cyano-N,N-dimethylaniline 

Downstream Products

• 55100-49-7 2-Hydroxymethyl-N-methyl-N-phenyl-butyramide 
• 63017-93-6 N-Methyl-N-phenyl-2-(methylthio)butyramid 
• 63017-92-5 N-Methyl-N-phenyl-2,2-bis(methylthio)butyramid 
• 93766-63-3 5-Benzenesulfinyl-2-ethyl-3-hydroxy-3-methyl-pentanoic acid methyl-phenyl-amide 
• 144691-19-0 2-Ethyl-3-(N-methyl-N-phenylamino)-2H-azirine 
• 92173-30-3 5-Benzenesulfinyl-2-ethyl-pentanoic acid methyl-phenyl-amide 
• 144691-23-6 N²-2-(Benzyloxycarbonyl)glycyl>-2-ethyl-N¹-methyl-N¹-phenylglycine-amide 
• 144691-27-0 N-<1-(N-Methyl-N-phenylthiocarbamoyl)propyl>benzamide 
• 94736-81-9 5-Benzenesulfinyl-2-ethyl-3-hydroxy-pentanoic acid methyl-phenyl-amide 
• 53101-23-8 N-Methyl-N-phenyl-2-ethyl-octanoamid 

Relevant academic research and scientific papers

Cross-Dehydrogenative Cyclization-Dimerization Cascade Sequence for the Synthesis of Symmetrical 3,3′-Bisoxindoles

The synthesis of symmetrical 3,3′-bisoxindoles from simple acyclic β-oxoanilides is reported. The described method forges three new C-C bonds in a single step via a sequential Mn(OAc)3·2H2O mediated oxidative radical cyclization-fragmentation-dimerization process. The scope of this reaction is demonstrated in the preparation of a variety of 3,3′-bisoxindoles, as well as its application toward the formal synthesis of the Calycanthaceae alkaloid, (±)-folicanthine.

N-Heterocyclic Carbene/Cobalt Cooperative Catalysis for the Chemo- and Regioselective C?N Bond Formation between Aldehyde and Amines/Amides

A novel methodology for the construction of various secondary (4 examples), tertiary amides (31 examples), and imides (16 examples) by a Cobalt(II) catalyzed oxidative amide coupling in aqueous media. The Co(III)-TMC was reacted with N-Heteroatom Carbene to form active catalyst Co(II)NHC-TMC in situ which involves in the coordination with Breslow's intermediate and SET for the activation of aldehyde and amides. The mechanism for activation of amide and amine differs on the basis of SET based nucleophilic addition and ligand exchange respectively. The regeneration of the catalyst was achieved using Fe(III)(EDTA)-H2O2 as oxidant. The use of Co(II)TMC-O2 was also found equally efficient in the process. The method is found regioselective for N?H activation in the presence of equally susceptible ortho-C?H bond activation. And amines were found more susceptible then the corresponding amide for the reaction.

Facile amidation of esters with aromatic amines promoted by lanthanide tris (amide) complexes

The development of catalysts capable of catalyzing amidation of esters with amines to construct amides under mild conditions is of great importance. Compared to aliphatic amines, the direct catalytic amidation of esters with less nucleophilic aromatic amines is rather difficult. Employing simple lanthanide tris (amide) complexes Ln[N (SiMe3)2]3(μ-Cl)Li (THF)3 as the catalysts, it was found a broad range of aromatic amines and esters were efficiently converted into various amides in good yields under mild conditions. A plausible mechanism for this transformation was experimentally supported as starting from an amide exchange reaction between the lanthanide tris (amide) complex and the substrate amine.

An efficient synthesis of benzothiazole using tetrabromomethane as a halogen bond donor catalyst

An efficient and mild protocol has been developed for the synthesis of 2-substituted benzothiazole under solvent- and metal-free conditions using CBr4 as the catalyst. This process involves the activation of a thioamide through halogen bond formation between the sulphur atom of the thioamide and bromine atom of the CBr4 molecule. The presence of halogen-bonding interaction between N-methylthioamides and tetrabromomethane has been demonstrated with several control experiments, spectroscopic analysis and density functional theory (DFT). This methodology has a wide substrate scope for the synthesis of both 2-alkyl and 2-aryl substituted benzothiazoles.

Amide Bond Formation Catalyzed by Recyclable Copper Nanoparticles Supported on Zeolite Y under Mild Conditions

A series of catalysts based on supported copper nanoparticles have been prepared and tested in the amide bond formation from tertiary amines and acid anhydrides, in the presence of tert-butyl hydroperoxide as an oxidant. Copper nanoparticles on zeolite Y (CuNPs/ZY) was found to be the most efficient catalyst for the synthesis of amides, working in acetonitrile as solvent, under ligand- and base-free conditions in air. The products were obtained in good to excellent yields and in short reaction times. The CuNPs/ZY system also exhibited higher catalytic activity than some commercially available copper and iron sources and it was reused in ten reaction cycles without any further pre-treatment. This methodology has been successfully scaled-up to a gram scale with no detriment to the yield.

Rapid Vortex Fluidics: Continuous Flow Synthesis of Amides and Local Anesthetic Lidocaine

Thin film flow chemistry using a vortex fluidic device (VFD) is effective in the scalable acylation of amines under shear, with the yields of the amides dramatically enhanced relative to traditional batch techniques. The optimized monophasic flow conditions are effective in ≤80seconds at room temperature, enabling access to structurally diverse amides, functionalized amino acids and substituted ureas on multigram scales. Amide synthesis under flow was also extended to a total synthesis of local anesthetic lidocaine, with sequential reactions carried out in two serially linked VFD units. The synthesis could also be executed in a single VFD, in which the tandem reactions involve reagent delivery at different positions along the rapidly rotating tube with in situ solvent replacement, as a molecular assembly line process. This further highlights the versatility of the VFD in organic synthesis, as does the finding of a remarkably efficient debenzylation of p-methoxybenzyl amines.

Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process

Abstract The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)2·H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method.

Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process

A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)2·H2O/KOtBu in DMF at 110 °C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.

Copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagents

The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.

Iron-catalyzed oxidative amidation of tertiary amines with aldehydes

Unconventional couple: A new oxidative coupling protocol for amide bond formation has been developed (see scheme). The method provides an efficient and practical route for the synthesis of tertiary amides from readily available tertiary amines and aldehydes in the presence of a simple FeCl2 catalyst. Mechanistic studies indicated that a peroxide and an iminium ion act as the reactive intermediates in this oxidative amidation.