Tag: 100-200

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

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

Total synthesis of antibiotic althiomycin was written by Inami, Kaoru;Shiba, Tetsuo. And the article was included in Bulletin of the Chemical Society of Japan in 1985.Quality Control of 2,2-Diethoxyacetamide This article mentions the following:

Total synthesis of antibiotic althiomycin (I) was achieved staring from D-cysteine. The imide bond between thiazoline and the pyrrolinone part was constructed by coupling reaction of sodium salt of pyrrolinone with cysteine active ester or by photoreaction with diketene. The hydroxymethyl group attached on the carbon adjacent to C-2 of the thiazoline ring, was introduced by aldol condensation posterior to the thiazoline ring formation. The thiazole part was introduced in a final step in whole process of the total synthesis of the antibiotic. The synthetic althiomycin was identical with the natural antibiotic in all respects. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Quality Control of 2,2-Diethoxyacetamide).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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.Quality Control of 2,2-Diethoxyacetamide

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

Mechanochemical Synthesis of Primary Amides was written by Gomez-Carpintero, Jorge;Sanchez, J. Domingo;Gonzalez, J. Francisco;Menendez, J. Carlos. And the article was included in Journal of Organic Chemistry in 2021.Electric Literature of C6H13NO3 This article mentions the following:

Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters RCOOEt (R = 3-fluorophenyl, 1,3-diethoxy-1,3-dioxopropan-2-yl, thiophen-2-yl, etc.) and 2-chromanone with ethanol and calcium nitride afforded the corresponding primary amides RC(O)NH₂in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodol. was applied to α-amino esters (S)-H₂NCH(CH₂R¹)C(O)OEt [R¹ = Ph, (methylsulfanyl)methyl] and N-Boc dipeptide esters (S)-(CH₃)₃COC(O)NHCH(CH₂R²)C(O)NHCH₂C(O)OEt (R² = H, Ph, 1H-indol-3-yl) and also to the synthesis of rufinamide, an antiepileptic drug. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Electric Literature of C6H13NO3).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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. 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.Electric Literature of C6H13NO3

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

A Ruthenium-Catalyzed Cyclization to Dihydrobenzo[c]phenanthridinone from 7-Azabenzonorbornadienes with Aryl Amides was written by Aravindan, Narasingan;Vinayagam, Varathan;Jeganmohan, Masilamani. And the article was included in Organic Letters in 2022.Computed Properties of C9H10FNO2 This article mentions the following:

An efficient ruthenium(II)-catalyzed tandem C-C/C-N bond formation with aryl amides and 7-azabenzonorbornadienes was developed to synthesize cis-fused dihydrobenzo[c]phenanthridinones. The amide group functions as a directing group as well as a leaving group and provided an easy access to the pharmaceutically useful benzo[c]phenanthridine alkaloids such as nitidine and fagaronine analogs. The present methodol. was compatible with various functional groups with respect to azabicyclic alkenes and aromatic amides. The reaction mechanism involving directing-group-assisted C-H activation was proposed and supported by the deuterium labeling studies. In the experiment, the researchers used many compounds, for example, 3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1Computed Properties of C9H10FNO2).

3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1) 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. 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.Computed Properties of C9H10FNO2

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

Condensed pyrimidine systems. XIII. Some amino-substituted derivatives of guanine and 6-thioguanine was written by Elion, Gertrude B.;Lange, William H.;Hitchings, George H.. And the article was included in Journal of the American Chemical Society in 1956.Synthetic Route of C6H7N3O This article mentions the following:

Crude 4,5-diamino-6-hydroxy-2-mercaptopyrimidine (100 g.) refluxed 2 hrs. with 500 cc. 90% HCO₂H, cooled, and filtered, the filter cake pressed dry, suspended in 200 cc. HCONH₂, heated 2 hrs. at 175-85°, cooled, and filtered, and the crude product (100.5 g.) dissolved in 2 l. N NaOH, filtered, and reprecipitated with glacial AcOH gave 90 g. 6-hydroxy-2-mercaptopurine (I). I (42 g.) in 250 cc. 2N NaOH treated slowly with stirring with 31.5 g. Me₂SO₄ at 25-40°, the mixture stirred 1 hr., kept at room temperature overnight, adjusted to pH 5 with glacial AcOH and chilled, and the precipitate washed with cold H₂O and dried at 110° gave 44 g. (98% pure) 6-hydroxy-2-methylthiopurine (II); it did not melt below 300°. II heated with 3-4 molar equivalents aliphatic amine 24 hrs. at 140° (48 hrs. at 160° with aromatic amines) in a sealed tube gave the corresponding 2-(substituted-amino)-6-hydroxypurines (IIa). The mixture with MeNH₂ evaporated to dryness in vacuo, the solid residue dissolved at room temperature in about 5 volumes H₂O and filtered, the filtrate adjusted with AcOH to pH 5, and the precipitate dissolved in 40 volume hot 0.3N HCl and reprecipitated with NH₄OH (pH 6) gave 37% 2-methylamino-6-hydroxypurine (III). A similar run with 14% MeNH₂ in MeOH gave a 65% yield. In the same manner was prepared the EtNH analog of III, in 30% yield from 33% aqueous EtNH₂. The reaction mixture from Me₂NH cooled, diluted with 3 volume MeOH, chilled, and filtered, and the residue recrystallized from 100 parts boiling H₂O gave 50% 2-Me₂N analog of III; in a run with 2 molar equivalents 12% Me₂NH in MeOH the yield was 61%. The mixture from PhNH₂ diluted with 20 volumes 1:1 absolute EtOH-Et₂O precipitated 56% PhNH analog (IV) of III. In the same manner was prepared the p-Cl derivative of IV in 35% yield. The mixture from piperidine (without solvent) diluted with about 4 parts H₂O, filtered, acidified to pH 5 with HCl, and filtered, the filtrate evaporated to dryness in vacuo, the residue treated with 50 parts 1:1 6N HCl-Me₂CO to give the HCl salt of the product, the filter residue extracted several times with 10 parts boiling H₂O, the extract chilled, filtered, and treated in the same manner, and the combined crude solid product recrystallized from 50 parts hot 6N HCl, treated with Darco, and diluted with an equal volume Me₂CO and chilled gave 33% 2-piperidino-6-hydroxypurine (V). A similar run with piperidine in EtOH gave 10% V; a 19% yield of V was obtained in a run with 4 molar equivalents piperidine in 2 molar equivalents concentrated HCl. The appropriate 2-(substituted-amino)-6-hydroxypurine refluxed 3 hrs. with 5 parts freshly pulverized P₂S₅ and 50 parts dry pyridine, the pyridine removed in vacuo, the residue heated 15-20 min. with 40 volume H₂O, cooled, diluted cautiously with an equal volume concentrated NH₄OH, chilled, and filtered, and the filtrate concentrated to a small volume in vacuo, adjusted to pH 5, and chilled gave the corresponding 2-(substituted-amino)-6-mercaptopurine (VI) (substituted-amino group, mole crystal water, and % yield given): MeNH, 0.25, 64; EtNH, 0.5, 45; Me₂N, 1, 52; PhNH, 1.5, 34; piperidino, 0.5, 51. The ultraviolet absorption maximum and min. of the IIa and VI at pH 1 and 11 are tabulated. In the experiment, the researchers used many compounds, for example, 3-Aminopicolinamide (cas: 50608-99-6Synthetic Route of C6H7N3O).

3-Aminopicolinamide (cas: 50608-99-6) 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.Synthetic Route of C6H7N3O

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

New metal compounds of sulfonamides as fungicides against plant pathogenic fungi was written by Badawi, A. M.;Salama, M. A.;Mahmoud, M. B.. And the article was included in Delta Journal of Science in 1991.Application In Synthesis of N-Isopropylbenzenesulfonamide This article mentions the following:

Copper, zinc, tin, cobalt and mercury complexes of N-iso-Pr benzenesulfonamide were synthesized and tested as fungicides for control of some plant pathogenic fungi. Structure-activity relationships were discussed. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Application In Synthesis of N-Isopropylbenzenesulfonamide).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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.Application In Synthesis of N-Isopropylbenzenesulfonamide

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

1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 4: Synthesis of N-1 acidic functionality affording analogues with enhanced antiviral activity against HIV was written by Lynch, Christopher L.;Hale, Jeffrey J.;Budhu, Richard J.;Gentry, Amy L.;Mills, Sander G.;Chapman, Kevin T.;MacCoss, Malcolm;Malkowitz, Lorraine;Springer, Martin S.;Gould, Sandra L.;DeMartino, Julie A.;Siciliano, Salvatore J.;Cascieri, Margaret A.;Carella, Anthony;Carver, Gwen;Holmes, Karen;Schleif, William A.;Danzeisen, Renee;Hazuda, Daria;Kessler, Joseph;Lineberger, Janet;Miller, Michael;Emini, Emilio A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.Computed Properties of C6H12N2O4 This article mentions the following:

A series of α-(pyrrolidin-1-yl)acetic acids I [R¹ = H, Me, Me₂CH, cyclopropyl, cyclobutylmethyl, cyclohexyl, Ph, etc.; R² = Ph(CH₂)₃, 4-FC₆H₄; R³ = H, HO] was prepared and investigated as selective and potent antivirals against HIV. Several of the pyrrolidine zwitterions demonstrated reasonable in vitro properties, enhanced antiviral activities and improved pharmacokinetic profiles over the lead pyrrolidine. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Computed Properties of C6H12N2O4).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) 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. 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 C6H12N2O4

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

Salicylamide in urine after intake of acetylsalicylic acid due to degradation of salicylic acid conjugates was written by Besserer, Kurt;Tiess, Detlef;Kala, Maria. And the article was included in Z Zagadnien Nauk Sadowych in 2000.Recommanded Product: N,N-Diethylsalicylamide This article mentions the following:

In addition to the well-known acetylsalicylic acid metabolites, salicylamide (SA) was detected in urine from healthy persons after intake of acetylsalicylic acid. SA was found in the Et₂O extracts of urine after alkalinization by ammonia solution SA was identified by gas chromatog.-mass spectrometry. Further examination showed that SA was present in urine only after alkalinization by ammonia solution and not after alkalinization by NaHCO₃ or Na₂CO₃. When dimethyl-, diethyl- or dibutylamine was used for the alkalinization of the urine, the corresponding salicylic acid dialkylamides were detected. Further anal. led to the conclusion that ester-type salicylic acid glucuronide conjugates undergo degradation by hydrolytic amination to form the corresponding amides. This gives the possibility of a specific demonstration of the presence of ester-type glucuronide conjugates. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Recommanded Product: N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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.Recommanded Product: N,N-Diethylsalicylamide

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

Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides was written by De, Subhadip;Yin, Junli;Ma, Dawei. And the article was included in Organic Letters in 2017.Application of 10268-06-1 This article mentions the following:

Cu₂O/N,N’-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramol. cross-coupling product. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Application of 10268-06-1).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) 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. 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 of 10268-06-1

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