Tag: 100-200

Some reactions of substituted 2-bromopyridines was written by Berrie, A. H.;Newbold, G. T.;Spring, F. S.. And the article was included in Journal of the Chemical Society in 1952.Recommanded Product: 3-Aminopicolinamide This article mentions the following:

2-Hydroxy-3-nitropyridine (I) (14 g.), added to 50 g. PBr₃ and 16 g. Br, heated 5 hrs. at 100°, cooled, treated dropwise with 100 cc. MeOH and then with 300 cc. H₂O, and extracted with boiling C₆H₆ and the residue from the C₆H₆ extracted with petr. ether (b. 60-80°), gives 10 g. 2-bromo-3-nitropyridine (II), m. 125°; the 5-Cl derivative of I yields 59% of the 5-Cl derivative (III) of II, m. 75°; the 5-Br derivative of I gives 80% of 2,5-dibromo-3-nitropyridine (IV), m. 93°. II (1 g.) and 10 cc. conductivity HCl in 10 cc. AcOH, refluxed 3 hrs., give 0.5 g. 2-hydroxy-3-nitropyridine (V), pale yellow, m. 224°; III yields 54% of the 5-Cl derivative (VI) of V, yellow, m. 235°; IV, HCl, and AcOH give 64% of the 5-Br derivative (VII) of V, pale yellow, m. 242°; 10 g. 2-amino-5-bromo-3-nitropyridine (VIII) in 25 cc. H₂SO₄ (d. 1.84) at 0°, treated with 6 g. NaNO₂ in 15 cc. H₂O, kept 30 min. at 0°, and diluted with 150 cc. H₂O, gives 6.05 g. VII. V (0.7 g.), 2 g. PCl₅, and 1.5 cc. POCl₃, heated 2 hrs. at 100°, give 0.2 g. 2-chloro-3-nitropyridine (IX), m. 101°; VI gives 52% 2,5-dichloro-3-nitropyridine (X), m. 43°; X results in 1.3 g. yield from 2-amino-5-chloro-3-nitropyridine. VII, PCl₅, and POCl₃ give 45% 5-bromo-2-chloro-3-nitropyridine (XI), m. 68° (51% from VIII). II (0.75 g.) and 0.7 g. CuCN, gradually heated to 150°, the pressure reduced to 1 mm., and the heat source removed after 15 sec., give 0.3 g. 3-nitropicolinonitrile (XII), m. 78°; III yields the 5-Cl derivative (XIII) of XII, m. 98°. IV gives 66% of the 5-Br derivative (XIV) of XII, m. 102°. 3-Amino-2-bromopyridine yields 32% 3-aminopicolinonitrile (XIVA), m. 149°; 5-Cl derivative (XIVB), m. 175°, 25%. XII (100 mg.) and 0.2 cc. H₂SO₄ (d. 1.84), heated 2 hrs. at 100°, give 50 mg. 3-nitropicolinamide (XV), m. 211°; XIII yields 55% of the 5-Cl derivative of XV, m. 230° and XIV gives-56% of the 5-Br derivative (XVA), m. 232-3° (decompn). II (1.45 g.), 2 g. Fe filings, and 12 cc. AcOH, heated 2 hrs. at 100°, diluted with 15 cc. H₂O, basified with 30% NaOH, and the cooled product extracted with CHCl₃, give 0.8 g. 3-amino-2-bromopyridine (XVI), m. 79°; 1.1 g. III yields 0.1 g. of the 2-Cl analog (XVII) of XVI, m. 79-80°; 1 g. XVI in 10 cc. HCl (d. 1.19), refluxed 3 hrs., gives 0.5 g. XVII. XV (20 mg.), 20 mg. Fe filings, and 0.12 cc. AcOH, heated 2 hrs. at 100°, give 10 mg. 3-aminopicolinamide (XVIII), m. 175-7°, sublimes at 100°/10^-1 mm.; 120 mg. XIVA and 0.24 g. concentrated H₂SO₄, heated 2 hrs. at 100°, give 10 mg. XVIII. XIII, reduced in AcOH with Fe, gives 67% of the 5-Cl derivative (XIX) of XVIII, m. 168°; XIVB yields 11% XIX; 5-Br derivative of XVIII, m. 168°, 72 and 18% yield, resp. XI gives 81% 3-amino-2-bromo-5-chloropyridine (XX), m. 142°, absorption maximum at 2520 and 3140 A. (ε 11,500 and 5700); IV gives 84% 3-amino-2,5-dibromopyridine (XXI), m. 153°; 2,5-di-Cl analog, m. 129°; it results in 87% on reduction of X and in 0.2-g. yield on refluxing 2 hrs. 0.5 g. 3-amino-5-bromo-2-chloropyridine (XXII) in 10 cc. concentrated HCl. Reduction of XI with Fe in AcOH gives 85% XXII, m. 131°, absorption maximum at 2510 and 3140 A. (ε 7200 and 4700); 1 part XXI and 20 parts concentrated HCl, refluxed 2 hrs., give 35% XXII; 2.82 g. IV, 7 g. Sn, and 30 cc. HCl, refluxed until solution results, give 0.2 g. XXII. 2-Amino-5-bromo-3-nitropyridine, reduced with Sn and HCl, gives 21% 2,3-diamino-5-bromo-4(6)-chloropyridine, m. 164° (quinoxaline derivative from phenanthraquinone, C₁₉H₉N₃ClBr, m. 270-2°). XXII (0.3 g.) in 10 cc. concentrated HCl, treated at 0° with 0.55 g. NaNO₂ in 1.5 cc. H₂O and then with 1.1 g. Cu, shaken 1 hr., almost neutralized with 30% NaOH, and the precipitate extracted with Me₂CO and the residue from the Me₂CO extracted with petr. ether, gives 100 mg. 5-bromo-2,3-dichloropyridine, m. 30-1°. XXI (1.26 g.) with NaNO₂ in concentrated H₂SO₄ gives 0.6 g. 2,5-dibromo-3-hydroxypyridine, m. 195-7°. XVA (12.1 g.) and KOBr give 7 g. 2-amino-5-bromo-3-nitropyridine, yellow, m. 205°. In the experiment, the researchers used many compounds, for example, 3-Aminopicolinamide (cas: 50608-99-6Recommanded Product: 3-Aminopicolinamide).

3-Aminopicolinamide (cas: 50608-99-6) 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.Recommanded Product: 3-Aminopicolinamide

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

Hydrolysis of naptalam and structurally related amides: inhibition by dissolved metal ions and metal (hydr)oxide surfaces was written by Huang, Ching-Hua;Stone, Alan T.. And the article was included in Journal of Agricultural and Food Chemistry in 1999.Synthetic Route of C11H15NO2 This article mentions the following:

In metal ion-free solutions, the secondary amide naptalam hydrolyzes more rapidly as the pH is decreased; intramol. nucleophilic attack by a carboxylate side group is very likely involved. Millimolar levels of dissolved Cu^II and Zn^II inhibit hydrolysis between pH 3.6 and pH 6.5. Metal ion-naptalam complex formation is important since addition of the competitive ligand citrate lessens the inhibitory effect. The metal (hydr)oxide surfaces Al₂O₃ and FeOOH inhibit naptalam hydrolysis to a lesser degree; inhibition is proportional to the extent of naptalam adsorbed. Secondary amides (propanil, salicylanilide, and N-1-naphthylacetamide) and tertiary amides (N-methyl-N-1-naphthylacetamide, furalaxyl, and N,N-diethylsalicylamide) that lack carboxylate side groups do not hydrolyze within 45 days of reaction, even when millimolar Cu^II concentrations are present. Tertiary amides possessing carboxylate side groups (N,N-diethyl-3,6-difluorophthalamic acid and N,N-dimethylsuccinamic acid) do hydrolyze but are insensitive to the presence or absence of Cu^II. The inhibitory effect is believed to occur via metal coordination of (1) the carbonyl group of naptalam, which induces deprotonation of the amide group and makes the substrate less reactive toward nucleophilic attack; (2) the free carboxylate group of naptalam, which blocks intramol. nucleophilic attack; or (3) a combination of the two. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).

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.Synthetic Route of C11H15NO2

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

Improved chromatographic method for purification of lactoperoxidase from different milk sources was written by Koksal, Zeynep;Usanmaz, Hande;Bayrak, Songul;Ozdemir, Hasan. And the article was included in Preparative Biochemistry & Biotechnology in 2017.Application of 53297-70-4 This article mentions the following:

Our previous studies showed that sulfanilamide is a new competitive inhibitor of and can be used in the purification of lactoperoxidase (LPO, EC1.11.1.7) from milk. However, this method has some disadvantages like a lower purification factor. The aim of the present study is to improve the purification process of milk LPO from different sources. For this purpose, 16 com. sulfanilamide derivatives were selected for inhibition studies to determine the best inhibitor of bovine LPO by calculating kinetic parameters. A cyanogen bromide-activated Sepharose 4B affinity matrix was synthesized by coupling with each competitive inhibitor. Among the inhibitors, 5-amino-2-methylbenzenesulfonamide and 2-chloro-4-sulfamoylaniline were used as ligands for the purification of LPO from bovine, buffalo, cow, and goat milks with 1059.37, 509.09, 232.55, and 161.90, and 453.12-, 151.86-, 869.00-, and 447.57-fold, resp. Our results show that 5-amino-2-methylbenzenesulfonamide, 2-chloro-4-sulfamoylaniline, and 5-amino-1-naphthalenesulfonamide are the best inhibitors for one-step purification of the enzyme. In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Application of 53297-70-4).

4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4) 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)Nâ€?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 cmâˆ?. 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 53297-70-4

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

High-performance liquid chromatographic control of drugs containing caffeine was written by Alary, J.;Vergnes, M. F.. And the article was included in Annales Pharmaceutiques Francaises in 1984.Category: amides-buliding-blocks This article mentions the following:

Pharmaceutical dosage forms containing caffeine (I) [58-08-2] and other drugs were analyzed by reversed-phase HPLC. All the dosage forms except the oral solutions were extracted with CHCl₃ or water and I was determined at 273 nm. The mobile phase was a mixture of MeCN-HOAc (either 10:90 or 50:50). The other drugs were detected either at 273 nm or other wavelengths. The oral solutions were measured directly. The recovery was 98-100%. The method is applicable to various pharmaceutical forms. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Category: amides-buliding-blocks).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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.Category: amides-buliding-blocks

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

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both In Vitro and In Vivo was written by Zhang, Han;Yu, Peilin;Lin, Hongwei;Jin, Zefang;Zhao, Siqi;Zhang, Yi;Xu, Qingxia;Jin, Hongwei;Liu, Zhenming;Yang, Wei;Zhang, Liangren. And the article was included in Journal of Medicinal Chemistry in 2021.HPLC of Formula: 13255-50-0 This article mentions the following:

The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiol. approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 (I) exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, I was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0HPLC of Formula: 13255-50-0).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) 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)Nâ€?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 cmâˆ?. 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.HPLC of Formula: 13255-50-0

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

Directed hydroxylation of aromatics was written by Parker, Kathlyn A.;Koziski, Kathleen A.. And the article was included in Journal of Organic Chemistry in 1987.Name: N,N-Diethylsalicylamide This article mentions the following:

Regiospecific hydroxylation of an aromatic ring was accomplished by directed lithiation followed by oxygenation. Thus, EtCHMeLi was added to benzamide I (R = H) and Me₂NCH₂CH₂NMe₂ in THF. Then O was bubbled through the mixture to give 52% I (R = OH). In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Name: N,N-Diethylsalicylamide).

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

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

Solubilizing agents. V. Pyridinecarboxamides was written by Samejima, Masayoshi. And the article was included in Yakugaku Zasshi in 1960.Synthetic Route of C11H15NO2 This article mentions the following:

2-HO₂CC₅H₄N.HCl (120 g.) in 313 g. MeOH and 150 g. concentrated H₂SO₄ refluxed 5 hrs., the MeOH removed, the residue neutralized with Na₂CO₃, and the product extracted with C₆H₆ gave 117 g. 2-MeO₂CC₅H₄N, b₁₁ 109-11°. Li (20.9 g.) in 1200 ml. Et₂O treated dropwise with 58 ml. PhBr, 139.7 g. 2-MeC₅H₄N added dropwise, the mixture refluxed 30 min., the product poured onto 1000 g. solid CO₂, the Et₂O removed, the residue in 1200 ml. EtOH at 0° saturated with dry HCl gas, the EtOH removed, the residue in 750 ml. CHCl₃, 338 g. K₂CO₃, and 188 g. H₂O heated, and the CHCl₃ layer distilled gave 83.1 g. 2-EtO₂CCH₂C₅H₄N, b₆ 109-12°. 3-HO₂CC₅H₄N (61.8 g.) and 47.1 g. PhOH heated at 110-20°, the mixture treated dropwise with 76.7 g. POCl₃, heated at 130-40° until evolution of HCl gas ceased, the product poured into ice H₂O, neutralized with Na₂CO₃, and extracted with C₆H₆ gave 67.5 g. 3-PhO₂CC₅H₄N, m. 71-2° (EtOH-petr. ether). The above esters and 4-MeO₂CC₅H₄N treated with NH₄OH or amines and the products distilled gave x-RHNOCC₅H₄N (I) (x, R, % yield, and b.p./mm. or m.p. given): 2, H, 90, 105-6°; 2, Me, 77, 118-20°/4; 2, Et, 90, 128-9°/4; 2, Bu, 86, 122-3°/2; 2, HOC₂H₄, 69, 190-1°/4; 3, Me, 71, 104-5°; 3, Et, 89, 146-7°/3; 3, Bu, 85, 173-4°/3.5; 3, HOC₂H₄, 71, 90-1° 4, H, 86, 133-4°; 4, Me, 73, 113-14°; 4, Et, 69, 65-6°; 4, Bu, 84, 155-6°/1; 4, HOC₂H₄, 70, 133-4°. 2-RNHOCH₂CC₅H₄N (II) (R, % yield, b.p./mm. or m.p. given): H, 77, 118-20°; Me, 78, 137°/1; Et, 67, 61-2°; HOC₂H₄, 67, 94-5°. 3-PhO₂CC₅H₄N (10 g.) and 5 g. PhNH₂ (or 2-H₂NC₅H₄N) fused 3 hrs. at 200-10°, the PhOH removed in vacuo, and the product extracted with Et₂O gave 3-RNHOCC₅H₄N (III) (R, % yield, and m.p. given): Ph, 67, 122-3°; 2-pyridyl, 79, 139-41°. Solubilization effects of I, II, and III were studied by use of adrenochrome monosemicarbazone (IV), o-HOC₆H₄CONH₂ (V), p-MeC₆H₄NH₂ (VI), and caffeine (VII). There was practically no difference by the position in isomers of I. II showed increased solubilization activity, the effect being better in lower homologs with Me and Et groups. III was found to give a far stronger effect, while introduction of two alkyls into the N in the acid amide group resulted in increased solubility in the case of V and VI, but 30-40% decrease in the case of IV and VII. II showed a lowering of solubilization activity by 10-40% compared to 3-H₂NOCC₅H₄N. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).

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. 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.Synthetic Route of C11H15NO2

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

Activity coefficients of sulfurous compounds in different extractants was written by Pais, M. A.;Bondarenko, M. F.;Abramovich, Z. I.;Kruglov, E. A.. And the article was included in Neftekhimiya in 1975.HPLC of Formula: 5339-69-5 This article mentions the following:

The activity coefficients of sulfur compounds such as cyclo- and dialkyl sulfides (I), mercaptans (II), and alkylthiophenes (III) in 10 extractants were determined by gas-liquid chromatog. The relative separation selectivities of the S compounds and hydrocarbons were calculated The separation selectivities decreased in the following order: III �alkylbenzenes (IV) �I > normal-paraffins > II. The activity coefficients of cyclic S compounds such as thiophane (V) and III varied with temperature increase in a manner similar to that shown by the corresponding IV in the same extractants. Thus, the activity coefficients of IV, V, and III increased in sulfolane [126-33-0] and tricresyl phosphate [1330-78-5] with increasing temperature In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5HPLC of Formula: 5339-69-5).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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 can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.HPLC of Formula: 5339-69-5

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

Molecular features of sulfonamide transport in renal excretory processes was written by Despopoulos, Agamemnon;Callahan, Paul X.. And the article was included in American Journal of Physiology in 1962.Computed Properties of C7H10N2O2S This article mentions the following:

Renal tubular excretory transport of selected sulfonamides is assumed to require a physicochem. interaction between the substrate and a postulated intracellular receptor mol. It is proposed that substrate specificity in this transport system depends on the presence of the intramolecular sequence, SO₂N^–, in the sulfonamide. Reactivity of this group requires ionization at N, localization of the net neg. charge at N, and electronegativity at each O sufficient for the formation of H bonds. Presence of these 3 features in favorable combination permits transport. These proposals are supported by analysis of the physicochem., biochem., and physiol. behavior of 52 sulfonamides both in surviving rabbit renal cortical slices and in intact mongrel dogs. Although transport of sulfonamides is treated as an independent biochem. mechanism, its relation to the renal hippurate transport system is recognized and similar responses of both classes of substrates to probenecid or to acetate are demonstrated exptl. In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Computed Properties of C7H10N2O2S).

4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4) 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. 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.Computed Properties of C7H10N2O2S

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

New and convenient synthesis of acyl isocyanates was written by Speziale, A. J.;Smith, L. R.. And the article was included in Journal of Organic Chemistry in 1962.Electric Literature of C7H5Cl2NO This article mentions the following:

A new and convenient synthesis of acyl isocyanates (I) which involved the reaction of primary amides with oxalyl chloride (II) was described. A suspension of the amide in C₂H₄Cl₂ was treated with excess II, the mixture refluxed 4-16 h., evaporated, and I isolated by distillation in vacuo. The following I (RCONCO) were thus obtained (R, % yield, b.p./mm. given): ClCH₂, 64, 50-5°/20; Cl₂CH, 68, 135°/35; Cl₃C, 60, 80-5°/20; PhCH₂, 36, 85°/3; 3,4-Cl₂C₆H₃, 97, 105-5°/1.6; Ph, 75, 97-8°/23; Ph₂CH, 37, 136-40°/1.0-1.2. I were readily hydrolyzed on treatment with H₂O. Acyl ureas, carbamates, and thiocarbamates were formed on reaction with amines, alcs., and mercaptans. Diacyl ureas were isolated in small yield in some cases as side products.. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Electric Literature of C7H5Cl2NO).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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.Electric Literature of C7H5Cl2NO

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