Tag: 100-200

Phase-transfer-catalyzed N-alkylation of carboxamides and sulfonamides was written by Gajda, Tadeusz;Zwierzak, Andrzej. And the article was included in Synthesis in 1981.Application of 5339-69-5 This article mentions the following:

The conversion of PhCONH₂ to PhCONHR and PhCONR₂ (R = Et, Pr, Bu, Me₂CHCH₂, PhCH₂, Me₂CH) was catalyzed by Bu₄N⁺ HSO₄^– (I). A mixture of PhCONH₂, EtBr, NaOH, and I in C₆H₆ was refluxed to give PhCONHEt. Similarly prepared were EtCONHR¹ (R¹ = Et, Pr, Bu), PhSO₂N(R²)₂ (R² = Me, Et, Bu, PhCH₂, Me₂CH), and MeSO₂N(R³)₂ (R³ = Et, PhCH₂, Me₂CH). In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Application of 5339-69-5).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. 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.Application of 5339-69-5

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

Tf₂O-Mediated Intermolecular Coupling of Secondary Amides with Enamines or Ketones: A Versatile and Direct Access to β-Enaminones was written by Liu, Yong-Peng;Zhu, Cheng-Jie;Yu, Cun-Cun;Wang, Ai-E.;Huang, Pei-Qiang. And the article was included in European Journal of Organic Chemistry in 2019.Safety of 4-Formyl-N-isopropylbenzamide This article mentions the following:

Based on the Tf₂O-mediated intermol. reaction of secondary amides with enamines derived from ketones, a novel approach to β-enaminones was developed. The reaction is widely functional group tolerant and highly chemoselective. In the presence of 4 Å mol. sieves, the method can be extended to the one-pot condensation of secondary amides with ketones for NH β-enaminones synthesis. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Safety of 4-Formyl-N-isopropylbenzamide).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) 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. 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.Safety of 4-Formyl-N-isopropylbenzamide

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

Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A₄ hydrolase aminopeptidase inhibitors was written by Zhang, Fan;Wu, Dang;Wang, Gao-Lei;Hou, Shuang;Ping, Ou-Yang;Huang, Jin;Xu, Xiao-Yong. And the article was included in Chinese Chemical Letters in 2017.Formula: C7H7ClN2O This article mentions the following:

A series of novel 1,2,3-benzotriazin-4-one derivatives I [R = H, 6-O₂N, 7-Cl, etc.; X = (CH₂)_n; n = 0, 1, 2, 3, 4] were designed, synthesized and their inhibitory activities against leukotriene A4 hydrolase aminopeptidase in-vitro were evaluated. Many compounds showed moderate to good activities at the concentration of 10 μmol/L. Among them, compound I [R = 7-Cl; X = (CH₂)₄ (II)] exhibited the highest inhibitory activity up to 80.6% with an IC₅₀ of 1.30 ± 0.20 μmol/L. The compound II was also tested for the proliferation inhibitory activities in THP1 human AML cell line and its binding model with LTA4H enzyme by mol. docking was studied. It indicated that 1,2,3-benzotriazin-4-one was a promising scaffold for further study. The relationship between structure and inhibitory activity was also preliminarily discussed. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Formula: C7H7ClN2O).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. 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.Formula: C7H7ClN2O

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

Synthesis and properties of new 6,7-dimethoxy-3,4-dihydroand 1,2,3,4-tetrahydroisoquinolines. II. 1-Phenyl- and 1-benzyl- derivatives was written by Viel, Claude;Dorme, Regina;Rumpf, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1966.Application In Synthesis of 2-(2-Chlorophenyl)acetamide This article mentions the following:

Pharmacol. active papaverine analogs were prepd, o-ClC₆H₄CH₂Cl (100 g.), 50 g. KCN in 100 cc. H₂O, and 1l. EtOH was refluxed 7 hrs., the EtOH stripped and residue poured into 2 1. ice-H₂O to give 49 g. o-ClC₆H₄CH₂CN, b₂₄ 133-43°. The nitrile was hydrolyzed to o-ClC₆H₄CONH₂, m. 174°, and finally to o-ClC₆H₄CO₂H, m. 95°. Also prepared was o-FC₆H₄CO₂H (I), m. 59°. BzH was nitrated to give m-NO₂C₆H₄CHO (II), b₄ 114-23°, and 97 g. aldehyde was reduced with 95 g. KBH₄ in MeOH to give m-NO₂C₆H₄CH₂OH (III), b_1.5 140-2°. Prepared from III was m-NO₂C₆H₄CH₂Cl, m. 45-7° and from the chloride, m-NO₂C₆H₄CH₂CN, b_0.5 145-50°. mClC₆H₄COCl (76 g.) was reduced by the Rosenmund reaction to give 10 g. m-ClC₆H₄CHO (IV), b₂₃ 110-12°. II was reduced and the resulting m-NH₂C₆H₄CHO treated in situ by the Sandmeyer reaction to give IV. IV was condensed with hippuric acida zlactone to give 2-phenyl-4-(3-chlorobenzylidene)-5-oxazolone (V), m. 164°. V was refluxed with 10% NaOH and the resulting product treated with 130-volume H₂O₂ 2 hrs. to give 3 g. methyl 3 nitrophenylacetate, b₂₀ 125-30°. Similarly prepared were pClC₆H₄CH₂CN, b. 264-7°, and p-ClC₆H₄CH₂CO₂H, m. 106°. 3,4-Dimethoxy-β-phenethylamine, b₂₂ 170° (picrate, m. 164.5-5.0°) and β-phenethylamine (VI), b₁₅ 93° (picrate m. 174°) were also prepared A mixture of 7.7 g. I and 6 g. VI was heated 3 hrs. at 180° to give 8.82 g. β-phenethyl-o-fluorophenylacetamide (VII), m. 102-3°. Similarly prepared were homoveratryl-o-chlorobenzamide, b₁ 180-5°, m. 90° homoveratryl-o-chlorophenylacetamide, m. 120° and homoveratryl-m-chlorophenylacetamide, m. 92°. VII (2.58 g.) in PhMe was cyclized by refluxing with 15 cc. POCl₃ 1.5 hrs. to give 3,4-dihydro-1-(o-fluorobenzyl)isoquinoline (VIII), m. 156-7°. Polyphosphoric acid was also used for cyclization. Similarly prepared were 3,4dihydro-1-(o-chlorobenzyl)isoquinoline, m. 148°; 6,7-dimethoxy 3,4-dihydro-1-(o-chlorophenyl)isoquinoline (HBr salt, m. 192°, picrate, m. 182°) and 6,7-dimethoxy-3,4-dihydro-1-(o-fluorobenzyl)isoquinoline; HBr salt m. 190° picrate m. 185°. VIII (530 mg.) in MeOH was reduced with 500 mg. NaBH₄ in aqueous MeOH to give 1,2,3,4-tetrahydro-1-(o-fluorobenzyl)isoquinoline, m. 192.5°. Similarly prepared were 6,7-dimethoxy-1,2,3,4-tetrahydro-1-(p-nitrophenyl)isoquinoline (HCl salts, m. 260°, picrate, m. 160°) and 6,7-dimethoxy-1,2,3,4-tetrahydro-1-(p-nitrobenzyl)isoquinoline; tartrate salt m. 132°. p-Chlorobenzylidenehomoveratrylamine (15 g.) was refluxed 1 hr. at 100° with 67 cc. 24% HCl to give 10 g. 6,7-dimethoxy-1,2,3,4-tetrahydro-1-(p-chlorophenyl)isoquinoline; HCl salt m. 230°. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Application In Synthesis of 2-(2-Chlorophenyl)acetamide).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) 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. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Application In Synthesis of 2-(2-Chlorophenyl)acetamide

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

Site-Selective C-H Amidation of 2-Aryl Quinazolinones Using Nitrene Surrogates was written by Kim, Saegun;Jeoung, Daeun;Kim, Kunyoung;Lee, Seok Beom;Lee, Suk Hun;Park, Min Seo;Ghosh, Prithwish;Mishra, Neeraj Kumar;Hong, Suckchang;Kim, In Su. And the article was included in European Journal of Organic Chemistry in 2020.Safety of 6-Chloro-2-aminobenzamide This article mentions the following:

The site-selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)-catalyzed C-H amidation of 2-aryl quinazolin-4(3H)-ones with a range of nitrene surrogates including dioxazolones, organic azides, and N-methoxyamides. Complete site-selectivity and functional group tolerance are observed Notably, the large-scale reaction and late-stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Safety of 6-Chloro-2-aminobenzamide).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. 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.Safety of 6-Chloro-2-aminobenzamide

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

The synthesis of proximal-benzolumazine, proximal-benzoxanthine, proximal-benzotheophylline and proximal-benzocaffeine was written by Schneller, Stewart W.;Christ, William J.. And the article was included in Journal of Heterocyclic Chemistry in 1981.Application of 54166-95-9 This article mentions the following:

Title compounds I and II (R = R¹ = H; R = R¹ = Me; R = Me, R¹ = H) were prepared by commencing with 2,6-Cl(H₂H)C₆H₃CONH₂ and proceeding via a variety of 5,6-disubstituted 2,4(1H,3H)-quinazolinediones. Methylation of II (R = Me, R¹ = H) gave III and II (R = R¹ = Me) in a ratio of 4:1. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Application of 54166-95-9).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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. 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 of 54166-95-9

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

Thionyl fluoride-mediated one-pot substitutions and reductions of carboxylic acids was written by Bolduc, Trevor G.;Lee, Cayo;Chappell, William P.;Sammis, Glenn M.. And the article was included in Journal of Organic Chemistry in 2022.Application In Synthesis of 3-Fluoro-N-methoxy-N-methylbenzamide This article mentions the following:

Thionyl fluoride (SOF₂) is an underutilized reagent that is yet to be extensively studied for its synthetic applications. We previously reported that it is a powerful reagent for both the rapid syntheses of acyl fluorides and for one-pot peptide couplings, but the full scope of these nucleophilic acyl substitutions had not been explored. Herein, we report one-pot thionyl fluoride-mediated syntheses of peptides and amides (35 examples, 45-99% yields) that were not explored in our previous study. The scope of thionyl fluoride-mediated nucleophilic acyl substitutions was also expanded to encompass esters (24 examples, 64-99% yields) and thioesters (11 examples, 24-96% yields). In addition, we demonstrate that the scope of thionyl fluoride-mediated one-pot reactions can be extended beyond nucleophilic acyl substitutions to mild reductions of carboxylic acids using NaBH₄ (13 examples, 33-80% yields). In the experiment, the researchers used many compounds, for example, 3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1Application In Synthesis of 3-Fluoro-N-methoxy-N-methylbenzamide).

3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1) 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. 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.Application In Synthesis of 3-Fluoro-N-methoxy-N-methylbenzamide

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

Potential radioprotective agents-V. Melatonin analogs. Oral activity of p-aminopropiophenone and its ethylene ketal was written by Blickenstaff, Robert T.;Reddy, Shailaja;Witt, Robert. And the article was included in Bioorganic & Medicinal Chemistry in 1994.Category: amides-buliding-blocks This article mentions the following:

Seven new amides of 5-methoxytryptamine were synthesized and tested for radioprotective activity in mice. One of them, the heptafluorobutyramide 4, is moderately active (57% survivors); the rest demonstrate little or no activity. Of twelve compounds that had been found to exhibit high radioprotective activity by i.p. injection, only two [p-aminopropiophenone (9) and its ethylene ketal 8] retain that high activity (92-95% survivors) when administered orally. Three are moderately active: p-aminobenzonitrile (10, 55%), 5-methoxytryptamine octanoic amide (11, 50%), and p-aminobenzophenone (12, 48%). In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Category: amides-buliding-blocks).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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 are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Category: amides-buliding-blocks

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

Phytotoxicity and selectivity of action of a homologous series of N-alkyl- and N,N-dialkyl-3,4-dichlorobenzamides was written by Baruffini, A.;Pagani, G.;Caccialanza, G.;Gialdi, F.. And the article was included in Farmaco, Edizione Scientifica in 1971.Recommanded Product: 3,4-Dichlorobenzamide This article mentions the following:

Of the 45 N-alkyl- and N,N-dialkyl-3,4-dichlorobenzamides (I) prepared by usual methods and tested for pre- and post-emergence phytotoxicity against common weeds, N,N-di-sec-butyl-3,4-dichlorobenzamide (6 kg/ha) selectively inhibited the growth of Echinochloa crus-galli and Setaria glauca. Most compounds were inactive in pre-emergence tests, while in the post-emergence tests some activity was shown by N-sec-amyl-3,4-dichlorobenzamide, N-sec-butyl-3,4-dichlorobenzamide, and 3,4-dichloro-N-ethylbenzamide. The N-monoalkyl-3,4-dichlorobenzamides generally showed limited action only through foliar absorption, while the more active N-dialkyl-3,4-dichlorobenzamides were absorbed through both leaves and roots. In both cases, the degree of absorption and activity is related to the structure of the alkyl residue on the N, particularly in the case of the dialkyl compounds In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Recommanded Product: 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Recommanded Product: 3,4-Dichlorobenzamide

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

Determination of primary amines by benzenesulfonylation/GC with flame photometric detection was written by Ohrui, Satoshi;Kataoka, Hiroyuki;Miyamoto, Yoshiaki;Ohtsuka, Kimiyo Takeda;Nakita, Masami. And the article was included in Bunseki Kagaku in 1991.Name: N-Isopropylbenzenesulfonamide This article mentions the following:

A selective and sensitive GC (gas chromatog.) method is described for the determination of primary amines. After benzenesulfonylation of by the Hinsberg reaction, primary amines were completely separated from secondary amines by extraction with hexane in 50% KOH-22.5% MeOH solution Benzenesulfonyl derivatives of primary amines in acidic aqueous layer were extracted by Et₂O and determined by GC with flame photometric detection (FPD-GC) using a DB-1 capillary column. The FPD-GC calibration curves of amines were linear in the range of 20-1000 ng for the derivatives and the detection limits were about 10-100 pg as injection amounts This was >20 times more sensitive than the results obtained by GC with flame ionization detection. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Name: N-Isopropylbenzenesulfonamide).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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 are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Name: N-Isopropylbenzenesulfonamide

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