Category: amides-buliding-blocks

Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant was written by Yoshimura, Akira;Middleton, Kyle R.;Luedtke, Matthew W.;Zhu, Chenjie;Zhdankin, Viktor V.. And the article was included in Journal of Organic Chemistry in 2012.Related Products of 10268-06-1 This article mentions the following:

Hofmann rearrangement of carboxamides to carbamates using Oxone as an oxidant can be efficiently catalyzed by iodobenzene. This reaction involves hypervalent iodine species generated in situ from catalytic amount of PhI and Oxone in the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) in aqueous methanol solutions Under these conditions, Hofmann rearrangement of various carboxamides affords corresponding carbamates in high yields. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Related Products of 10268-06-1).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Related Products of 10268-06-1

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Multi stage peroxide and activated peroxide bleaching of kenaf bast pulp was written by Zeinaly, Farhad;Shakhes, Jalal;Zeinali, Nooshin. And the article was included in Carbohydrate Polymers in 2013.Safety of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) This article mentions the following:

Soda-anthraquinone kenaf bast pulp (12.5 kappa number and 32% ISO brightness) has been bleached with multi stage peroxide bleaching process. Bleaching process was carried out in different sequences of peroxide stage without and with activator (tetraacetylethylenediamine, TAED) to about 80% ISO brightness. Full bleached pulp production with high brightness and viscosity and also, low COD and no adsorbable organic halogens (AOX) in effluent are the aims of this study. The effects of temperature, retention time, chem. charges, TAED/peroxide ratio and alkalinity have been studied in order to maximize the brightness gain at the lowest viscosity loss. H₂O₂ was activated as bleaching agent under milder conditions, such as low alkalinity or low temperature, by TAED activator. Therefore, TAED charge caused to an improvement in viscosity, pulp yield and effluent COD load. Pre-treatment with EDTA for 30 min and in acidic condition gave 2-4% gain in ISO brightness. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Safety of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Safety of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Sustainable synthesis of monodispersed gold nanoparticles from Phoenix dactylifera L. and in vivo anti-diabetic activity on Alloxan induced mice was written by Zahid, Rabbia;Rizvi, Syeda Nayab Batool;Qureshi, Zahid;Din, Muhammad Imran. And the article was included in Vibrational Spectroscopy in 2022.Formula: C23H28ClN3O5S This article mentions the following:

In the present study, gold nanoparticles biogenically synthesized from Date palm seeds (Phoenix dactylifera L.) were investigated for its anti-diabetic properties. About thirty-two albino mice were selected and 7 days of acclimatization were studied then they were randomly divided into 4 groups (I-IV) of 8 rats each. These groups were i.p. injected with 100 mg/Kg body weight of Alloxan monohydrate. The groups were labeled as a diabetic group, control group, diabetic group treated with standard drug Glibenclamide (100 mg/Kg body weight), and diabetic group treated with AuNPs (100 mg/Kg body weight). This treatment was performed for 28 days via oral administration. The results showed a significant decline in the concentration of their blood glucose level after 28 days of continuous administration of AuNPs. Addnl., AuNPs significantly recovered the damage done to pancreatic, renal, and hepatic tissues in Alloxan induced mice. Hence, AuNPs formed through Phoenix dactylifera L. has appreciable anti-diabetic outcome in preclin. settings. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Formula: C23H28ClN3O5S).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Formula: C23H28ClN3O5S

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Cross-Coupling of Secondary Amides with Tertiary Amides: The Use of Tertiary Amides as Surrogates of Alkyl Carbanions for Ketone Synthesis was written by Wang, Shu-Ren;Huang, Pei-Qiang. And the article was included in Chinese Journal of Chemistry in 2019.Computed Properties of C11H13NO2 This article mentions the following:

Herein, we reported the cross-coupling of secondary amides with tertiary amides, which provided a synthesis of ketones R¹C(O)R² [R¹ = Et, 2-thienyl, Ph, etc.; R² = i-Pr, i-Bu, cyclohexyl, etc.] under mild conditions and features the use of tertiary amides as surrogates of alkyl carbanions. The method relied on the coupling of enamines, generated from tertiary amides by catalytic partial reduction of tertiary amides with Vaska’s catalyst, with nitrilium ions, formed in-situ from secondary amides via activation with trifluoromethanesulfonic anhydride and on the subsequent deformylation. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Computed Properties of C11H13NO2).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Computed Properties of C11H13NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

One-pot sequential 1,2-addition, Pd-catalysed cross-coupling of organolithium reagents with Weinreb amides was written by Giannerini, M.;Vila, C.;Hornillos, V.;Feringa, B. L.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.COA of Formula: C9H10BrNO2 This article mentions the following:

An efficient sequential 1,2-addition/cross-coupling of Weinreb amides with two organolithium reagents is reported. This synthetic approach allows access to a wide variety of functionalized ketones in a modular way. The one-pot procedure presented here takes advantage of a kinetically stable tetrahedral Weinreb intermediate during subsequent Pd-catalyzed cross-coupling with the second organolithium reagent leading, within short reaction times and under mild conditions, to the formation of ketones in excellent overall yields. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2COA of Formula: C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.COA of Formula: C9H10BrNO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Physical and enzymatic properties of a new manganese peroxidase from the white-rot fungus Trametes pubescens strain i8 for lignin biodegradation and textile-dyes biodecolorization was written by Rekik, Hatem;Zarai Jaouadi, Nadia;Bouacem, Khelifa;Zenati, Bilal;Kourdali, Sidali;Badis, Abdelmalek;Annane, Rachid;Bouanane-Darenfed, Amel;Bejar, Samir;Jaouadi, Bassem. And the article was included in International Journal of Biological Macromolecules in 2019.Related Products of 10543-57-4 This article mentions the following:

A new manganese peroxidase-producing white-rot basidiomycete fungus was isolated from symptomatic wood of the camphor trees Cinnamomum camphora (L.) at the Hamma Botanical Garden (Algeria) and identified as Trametes pubescens strain i8. The enzyme was purified (MnP TP55) to apparent electrophoretic homogeneity and biochem. characterized. The specific activity and Reinheitzahl value of the purified enzyme were 221 U/mg and 2.25, resp. MALDI-TOF/MS anal. revealed that the purified enzyme was a monomer with a mol. mass of 55.2 kDa. The NH₂-terminal sequence of the first 26 amino acid residues of MnP TP55 showed high similarity with those of white-rot fungal peroxidases. It revealed optimal activity at pH 5 and 40 °C. This peroxidase was completely inhibited by sodium azide and potassium cyanide, suggesting the presence of heme-components in its tertiary structure. Interestingly, MnP TP55 showed higher catalytic efficiency, organic solvent-tolerance, dye-decolorization ability, and detergent-compatibility than that of horseradish peroxidase (HRP) from roots of Armoracia rustanica, manganese peroxidase from Bjerkandera adusta strain CX-9 (MnP BA30), and manganese peroxidase from Phanerochaete chrysosporium (MnP PC). Overall, the findings provide strong support for the potential candidacy of MnP TP55 for environmental applications, mainly the development of enzyme-based technologies for lignin biodegradation, textile-dyes biodecolorization, and detergent formulations. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Related Products of 10543-57-4).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Related Products of 10543-57-4

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung was written by Bauer, Adriano;Di Mauro, Giovanni;Li, Jing;Maulide, Nuno. And the article was included in Angewandte Chemie, International Edition in 2020.Application In Synthesis of 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung [e.g., I → II (71%, d.r. > 95:5) + III (8%, d.r. > 95:5) in presence of PhIO.MsOH and BF₃.OEt₂]. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Application In Synthesis of 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Application In Synthesis of 4-Bromo-N-methoxy-N-methylbenzamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chiral, Magnetic, and Photosensitive Liquid Crystalline Nanocomposites Based on Multifunctional Nanoparticles and Achiral Liquid Crystals was written by Poryvai, Anna;Smahel, Michal;Svecova, Marie;Nemati, Ahlam;Shadpour, Sasan;Ulbrich, Pavel;Ogolla, Timothy;Liu, Jiao;Novotna, Vladimira;Veverka, Miroslav;Vejpravova, Jana;Hegmann, Torsten;Kohout, Michal. And the article was included in ACS Nano in 2022.Application of 2387-23-7 This article mentions the following:

Nanoparticles serving as a multifunctional and multiaddressable dopant to modify the properties of liquid crystalline matrixes are developed by combining cobalt ferrite nanocrystals with organic ligands featuring a robust photosensitive unit and a source of chirality from the natural pool. These nanoparticles provide a stable nanocomposite when dispersed in achiral liquid crystals, giving rise to chiral supramol. structures that can respond to UV-light illumination, and, at the same time, the formed nanocomposite possesses strong magnetic response. We report on a nanocomposite that shows three addnl. functionalities (chirality and responsiveness to UV light and magnetic field) upon the introduction of a single dopant into achiral liquid crystals. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Application of 2387-23-7

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reaction of electrogenerated cyanomethyl anion with cyclohexylisocyanate: synthesis of N-(cyclohexylcarbamoyl)acetamide. An unexpected product was written by Scarano, Vincenzo;Bortolami, Martina;Pandolfi, Fabiana;Petrucci, Rita;Rocco, Daniele;Zollo, Giuseppe;Feroci, Marta. And the article was included in Journal of the Electrochemical Society in 2020.Reference of 2387-23-7 This article mentions the following:

The contamination with H₂O of the cathodic ACN-Et₄NBF₄ solution gave the authors the opportunity to study alkyl isocyanate reactivity toward electrogenerated anions. The cathodic reduction of a ACN-Et₄NBF₄ solution gave both hydroxide and cyanomethyl anions. The reaction of the catholyte with cyclohexylisocyanate led to the exclusive formation of acetamidated product, with no traces of cyanomethylated one. On the contrary, when reacting with benzaldehyde only the cyanomethylated was isolated. Considering that the acetamidated product of benzaldehyde is reported to be unstable (thus its formation cannot be excluded), various experiments were carried out to understand the anomalous reactivity of cyclohexylisocyanate. Also, computational anal. allowed to state the higher stability of acetamidated product with respect to the cyanomethylated one. The possibility of a concerted reaction, instead of acetamide anion formation prior to the reaction, is still an open question. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Reference of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Reference of 2387-23-7

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In vivo pharmacokinetic analyses of placental transfer of three drugs of different physicochemical properties in pregnant rats was written by Mehta, Darshan;Li, Miao;Nakamura, Noriko;Chidambaram, Mani;He, Xiaobo;Bryant, Matthew S.;Patton, Ralph;Davis, Kelly;Fisher, Jeffrey. And the article was included in Reproductive Toxicology in 2022.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Although the use of medication during pregnancy is common, information on exposure to the developing fetus and potential teratogenic effects is often lacking. This study used a rat model to examine the placental transfer of three small-mol. drugs with mol. weights ranging from approx. 300 to 800 Da with different physicochem. properties. Time-mated Sprague Dawley (Hsd:SD) rats aged 11-13 wk were administered either glyburide, rifaximin, or fentanyl at gestational day 15. Maternal blood, placentae, and fetuses were collected at 5 min, 30 min, 1 h, 4 h, 8 h, 24 h, 48 h, and 96 h post-dose. To characterize the rate and extent of placental drug transfer, we calculated several pharmacokinetic parameters such as maximum concentration (Cmax), time to maximum concentration (Tmax), area under the concentration-time curve (AUC), half-life (t1/2), clearance (CL), and volume of distribution (Vd) for plasma, placenta, and fetus tissues. The results indicated showed that fetal exposure was lowest for glyburide, accounting for only 2.2% of maternal plasma exposure as measured by their corresponding AUC ratio, followed by rifaximin (37.9%) and fentanyl (172.4%). The fetus/placenta AUC ratios were found to be 10.7% for glyburide, 11.8% for rifaximin, and 39.1% for fentanyl. These findings suggest that although the placenta acts as a protective shield for the fetus, the extent of protection varies for different drugs and depends on factors such as mol. weight, lipid solubility, transporter-mediated efflux, and binding to maternal and fetal plasma proteins. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics