7465-87-4

Usage

Uses

Used in Organic Synthesis:
BenzaMide, 4-Methoxy-N-(phenylMethyl)is used as a building block in organic synthesis for the creation of complex molecules. Its unique structure allows for the formation of various derivatives, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
BenzaMide, 4-Methoxy-N-(phenylMethyl)is utilized in pharmaceutical research as a starting material for the development of new drugs. Its potential therapeutic applications make it a promising candidate for the treatment of various medical conditions. Researchers can modify its structure to explore its efficacy and safety in different therapeutic areas.
Used in Drug Development:
BenzaMide, 4-Methoxy-N-(phenylMethyl)is employed in drug development to create novel therapeutic agents. Its unique chemical properties and potential medicinal applications make it an attractive candidate for the development of innovative drugs to address unmet medical needs.

InChI:InChI=1/C15H15NO2/c1-18-14-9-7-13(8-10-14)15(17)16-11-12-5-3-2-4-6-12/h2-10H,11H2,1H3,(H,16,17)

Upstream product

• 858790-28-0 3,7-bis-(4-methoxy-benzoyl)-2,8-bis-(4-methoxy-phenyl)-pyrano[3,2-g]chromene-4,6-dione 
• 100-46-9 benzylamine 
• 100-09-4 4-methoxybenzoic acid 
• 110-86-1 pyridine 
• 98-09-9 benzenesulfonyl chloride 
• 88-95-9 Phthaloyl dichloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 68-12-2 N,N-dimethyl-formamide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 4231-69-0 1-(4-methoxybenzoyl)-1H-1,2,3-benzotriazole 
• 68055-31-2 N-benzyl-4-methoxybenzenecarbothioamide 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 3424-93-9 4-methoxyphenylacetamide 
• 619-57-8 p-hydroxybenzamide 
• 876893-18-4 N-[(1H-1,2,3-benzotriazol-1-yl)(4-methoxyphenyl)methylidene]-N-benzylamine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 100-46-9 benzylamine 
• 1430730-41-8 4-benzyl-5-(4-methoxyphenyl)-3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole 
• 588-46-5 N-(phenylmethyl)acetamide 
• 26209-45-0 N-benzyl-2,2-dimethylpropanamide 
• 14309-88-7 N-benzylthioacetamide 
• 103197-90-6 N-benzyl-2,2-dimethylpropanethioamide 
• 3027-02-9 N-acetyl-N-benzylacetamide 
• 1598437-64-9 N-acetyl-N-benzyl-4-methoxybenzamide 
• 65551-44-2 2-(N-benzylamino)-2-(4-methoxyphenyl)acetonitrile 

Relevant academic research and scientific papers

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.

Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines

A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is

Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation

Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.

Metal-free selective reduction of acid chlorides to aldehydes using 1-hydrosilatrane

This work uses 1-hydrosilatrane – an accessible and easy-to-handle reducing reagent – to selectively reduce acid chlorides to aldehydes. This metal-free reduction proceeds rapidly at ambient temperature in the presence of N-methylpyrrolidine, efficiently producing aldehydes in up to 54% yield and with the balance largely remaining as starting material. No over-reduced alcohol product is observed.

Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides

The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.

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.

Palladium Catalyzed Direct Carbonylative Thiomethylation of Aryldiazonium Salts and Amines with 4-(Methylthio)-2-Butanone as (Methylthio) Transfer Agent

Herein, an interesting palladium-catalyzed procedure for the direct carbonylative thiomethylation of aromatic amine derivatives with 4-methylthio-2-butanone is developed. Using 4-methylthio-2-butanone as (methylthio) transfer agent, a variety of corresponding thioesters are obtained with moderate to good yields under base-free condition. In addition, good functional group tolerance can be observed.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.