68388-03-4

Basic information

• Product Name: N-(3-benzamidopropyl)benzamide
• CAS NO: 68388-03-4
• Molecular Formula: C₁₇H₁₈N₂O₂
• Molecular Weight: 282.342
• Mol File: 68388-03-4.mol

Chemical Properties

• Boiling Point: 588.7°Cat760mmHg
• Flash Point: 229°C
• Density: 1.14g/cm³
• CAS DataBase Reference: N-(3-benzamidopropyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-benzamidopropyl)benzamide(68388-03-4)
• EPA Substance Registry System: N-(3-benzamidopropyl)benzamide(68388-03-4)

Safety Data

• Hazardous Substances Data: 68388-03-4(Hazardous Substances Data)

Upstream product

• 871902-67-9 1-benzoylamino-3-dibenzoylamino-propane 
• 98-88-4 benzoyl chloride 
• 109-76-2 Trimethylenediamine 
• 65616-97-9 1,2-bisbenzoylpyrazolidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 65-85-0 benzoic acid 
• 848417-68-5 3,6-dibenzoyloxy-1,2-pyridazine 
• 25099-77-8 2-phenyl-1,4,5,6-tetrahydropyrimidine 
• 618-39-3 benzamidin 
• 10364-94-0 1-benzoylimidazole 
• 10517-44-9 1,3-diaminopropane dihydrochloride 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 15937-64-1 1,3-dibenzoylhexahydropyrimidine 
• 25099-77-8 2-phenyl-1,4,5,6-tetrahydropyrimidine 
• 21600-82-8 N,N'-dinitroso-N,N'-propanediyl-bis-benzamide 
• 93300-57-3 C₁₉H₂₂N₂O₂ 
• 70011-90-4 N,N'-1,3-propanediyl bisthiobenzamide 
• 10239-34-6 N,N'-dibenzyl-1,3-diaminopropane 
• 201996-36-3 1-benzoyl-2-phenyl-1,4,5,6-tetrahydropyrimidine 
• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 

Relevant articles and documents

Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2-CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated from the latter amides, namely RCONHCHO. Also, the anodic process was found to be more efficient with C felt as the anode, and in a mixture of 1:1 methanol/acetonitrile co-solvents.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Palladium-Catalyzed Direct Synthesis of Phenanthridones from Benzamides through Tandem N–H/C–H Arylation

We report a palladium-catalyzed method for the direct synthesis of phenanthridones from benzamides in a single step. Unlike previous reports, the current protocol does not need any directing groups or any harsh conditions. This methodology has a wide functional group tolerance therefore a series of phenanthridones were synthesized with a yield up to 87 %. The efficacy of this protocol was further explored by synthesizing some important naturally occurring amaryllidaceae alkaloids in a single step with very good yields.

One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70%) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65%) was obtained with 1,4-diaminobenzene as coupling amine, at 100°C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.

Structure-property relationships of aromatic polyamides and polythioamides: comparative consideration with those of analogous polyesters, polythioesters and polydithioesters

Conformational characteristics and configurational properties of aromatic polyamides and polythioamides, analogues of common aromatic polyesters such as poly(ethylene terephthalate) and poly(trimethylene terephthalate), have been investigated via NMR experiments and molecular orbital calculations on model compounds, and the refined rotational isomeric state calculations for the polymers. The polyamides and polythioamides were actually synthesized and characterized in terms of solubility, molecular weight, crystallinity, thermal transition, and thermal stability. Herein, the experimental results are discussed mainly from the viewpoint of the conformational characteristics and compared with those obtained from analogous aromatic polyesters, polythioesters, and polydithioesters to reveal the effects of the heteroatoms O, S, and NH included in the backbone on the polymer structures and properties.

Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors

In order to identify novel anti-hepatitis C virus (HCV) agents we devised cell-based strategies and screened phenotypically small molecule chemical libraries with infectious HCV particles, and identified a hit compound (1) containing a hexahydropyrimidine (HHP) core. During our cell-based SAR study, we observed a conversion of HHP 1 into a linear diamine (6), which is the active component in inhibiting HCV and exhibited comparable antiviral activity to the cyclic HHP 1. In addition, we engaged into the biological characterization of HHP and demonstrated that HHP does not interfere with HCV RNA replication, but with entry and release of viral particles. Here we report the results of the preliminary SAR and mechanism of action studies with HHP.

Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors

Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.

Stabilized well-dispersed Pd(0) nanoparticles for aminocarbonylation of aryl halides

Well-dispersed palladium (0) nanoparticles stabilized with phosphonium based ionic liquid were synthesized conveniently and fully characterized. A catalyst system comprising of the Pd(0) nanoparticles and a base was found to be recyclable and efficient for the aminocarbonylation reaction of aryl iodide in ionic liquid media. In the presence of potassium tert-butyloxide, for the relatively stable aryl chloride and bromide substrates, medium activities were achieved for the catalyst. The catalyst composites can be recycled at least five times with sustained activity.

Inclusion compound of β-cyclodextrin with binuclear guests containing residues of some pharmocologically important aromatic monocarboxylic acids

Stable monomeric and dimeric inclusion compounds of β-cyclodextrin with binuclear guests containing the residues of some pharmacologically important aromatic monocarboxylic acids were obtained. Pleiades Publishing, Ltd., 2011.

Imidazole-catalyzed monoacylation of symmetrical diamines

Figure Presented. An imidazole-catalyzed protocol for monoacylation of symmetrical diamines has been developed. The protocol gave selective monoacylation of aliphatic (cyclic and acyclic) primary and secondary diamines. In the reaction, imidazole acts as both catalyst and a leaving group. Different monoacylated piperazines and other diamines were synthesized at room temperature in an ethanol/water solvent system.