Category: 83909-69-7

A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water was written by Balkrishna, Shah Jaimin;Kumar, Sangit. And the article was included in Synthesis in 2012.Reference of 83909-69-7 The following contents are mentioned in the article:

An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides was described from 2-chlorobenzamide substrates using CuI/1,10-phenanthroline and a base, KOH, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups, such as F, Cl, I, MeO, amide, and alc., were obtained in 33-96% yield. Other aromatic 2-chloroarylamides, such as naphthalene, pyridine, and thiophene, are equally compatible to the reaction. It is proposed that the reaction proceeds via formation of a copper-amide complex, which may facilitate the hydroxylation in water. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. This study involved multiple reactions and reactants, such as N-Benzyl-2-chloro-5-nitrobenzamide (cas: 83909-69-7Reference of 83909-69-7).

N-Benzyl-2-chloro-5-nitrobenzamide (cas: 83909-69-7) 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.Reference of 83909-69-7

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

Preparation of 5-nitroisothiazolone and derivatives was written by Ponci, R.;Baruffini, A.;Croci, M.;Gialdi, F.. And the article was included in Farmaco, Edizione Scientifica in 1963.Safety of N-Benzyl-2-chloro-5-nitrobenzamide The following contents are mentioned in the article:

Adding a solution of KOH in EtOH with stirring to 80 g. 2,5-Cl(O₂N)C₆H₃CO₂H (I) in 300 cc. EtOH and concentrating to dryness at 40° gave I K salt. Powd. and dried I K salt (24 g.) was suspended in 220 cc. absolute EtOH, the mixture heated to boiling, 0.05 mole freshly prepared Na₂S₂ in 96% EtOH added with stirring in 90 min., and the mixture heated 1 hr. to give 65-70% yellow [2,4-HO₂C(O₂N)C₆H₃]₂S (II), m. 280° (decomposition) (AcOH). A suspension of 6 g. II in anhydrous PhMe and 7 g. PCl₅ was refluxed 2.5 hrs. to give 6.5 g. yellow [2,4-ClOC(O₂N)C₆H₃]₂S (III), m. 229-30° (dioxane). III was converted with refluxing absolute EtOH to [2,4-EtO₂C(O₂N)C₆H₃]₂S, m. 169° (benzene-petr. ether). Powd. 2,5-Cl(O₂N)C₆H₃CO₂H was covered with SOCl₂ and the mixture refluxed 1.5 hrs. to give 90% 2,5-Cl(O₂N)C₆H₃COCl (IV), m 60-1° (ligroine). IV was converted to the following 2,5-Cl(O₂N)C₆H₃CONHR (V) with a dioxane solution of the appropriate amine (or by bubbling in NH₃) (R and m.p. given): H, 178°; Ph, 158°; Bu, 136°; PhCH₂, 195°; 3-pyridylmethyl, 201°. III and a dioxane solution of the appropriate amine (method A) or 0.02 mole V and 0.01 mole freshly prepared Na₂S₂ in EtOH refluxed 90 min. (method B) gave the following: [2,4-ROC(O₂N)C₆H₃]₂S (VI) (method, R, and m.p. given): A, NH₂, 250° (decomposition); A, MeNH, 255° (decomposition); A or B, BuNH, 215-18°; B, PhCH₂NH, 243-5°; A, piperidino, 183°; A or B, PhNH, 241-3°; A, p-ClC₆H₄NH, >230° (decomposition); A or B, 3-pyridylmethylamino, 194-5°. Treating V (R = PhCH₂NH) (VII) with an equivalent amount of Na₂S₂.9H₂O gave 2,5-EtO(O₂N)C₆H₃CONHCH₂Ph (VIII), m. 151° (EtOH), which was also obtained directly from VII and alc. NaOH. VII and methanolic NaOH gave 2,5-MeO(O₂N)C₆H₃CONHCH₂Ph, m. 108° (benzene-petr. ether). Heating 1 mole 2,5-EtO(O₂N)C₆H₃COCl, m. 80° (prepared from the corresponding acid, m. 161-3°, and SOCl₂) with 2 moles PhCH₂NH₂ in 10% dioxane 20 min. at 50° gave VIII. III (5 g.) in 150 cc. anhydrous (CHCl₂)₂ was treated with 4 cc. Br, the mixture refluxed 90 min., excess Br removed in vacuo, the solution concentrated to half volume, anhydrous CCl₄ added in 2 80-cc. portions, and the solution concentrated to 70 cc., and filtered. Then, 12 cc. 20% aqueous NH₃ was introduced slowly with vigorous stirring at <20°, and the mixture kept 2 hrs. at ambient temperatures to give about 3 g. yellow IX (R = H), m. >280° (AcOH) (method C). Refluxing 1 g. VI(R = NH₂) in 50 cc.(CHCl₂)₂ with 1.5 cc. Br 6 hrs. gave 0.4 g. IX (R = H) (method D). The following IX were thus prepared (method, R, and m.p. given): C or D, Me, 229-30°; C or D, PhCH₂, 142°; C or D, Ph, 228°; C, p-C₆H₄Cl, 215-17°; C, Bu, 79°. The last compound was also prepared by suspending 2.17 g. III in 40 cc. anhydrous (CHCl₂)₂, adding 6 drops of 20% oleum, and heating at 50-60° while introducing a fast stream of Cl. The excess Cl was removed in a stream of dry N and the filtered solution dropped into 20 cc. anhydrous CCl₄ containing 4.4 g. BuNH₂. After standing 1 hr. at ambient temperatures, the mixture was extracted with very cold dilute HCl and then washed with H₂O. The identity of IX was confirmed by conversion to the corresponding 5-nitrosaccharins (X). To a suspension of 3 g. IX (R = H) in 30 cc. AcOH was added 10 cc. 30% H₂O₂ and the mixture heated 60 min. at 100° to give X (R = H), m. 213-16° (method E). An ethereal solution of 2 g. 2,4-Cl(O₂N)C₆H₃SO₂Cl was dropped with stirring into 5 cc. 20% NH₃ with cooling. The mixture was kept 2 hrs. at ambient temperatures, concentrated, and dried in vacuo at low temperature A 1-g. portion of the residue was dissolved in 100 cc. H₂O, passed through a 2-cm. diameter column containing 40 g. Amberlite C.G. 120 activity, and eluted with 150 cc. H₂O to give X (R = H) (method F). X (R = Na) (1 g.) in 5 cc. HCONMe₂ was heated slowly to reflux with 2 equivalents MeI and the mixture refluxed 15 min. to give 70% X (R = Me) (method G). The following X were also prepared (method, R, and m.p. given): E, Me, 170°; E or G, Bu, 74°; E or G, PhCH₂, 139°; E or F, Ph, 203°; E, p-C₆H₄Cl, 181°. Dried and powd. 7 g. II was added in small portions with stirring to 50 cc. HNO₃ (d. 1.52) kept at 0°, the mixture kept 30 min. with stirring at ambient temperatures, and 100 cc. 10% K₂CO₃ added dropwise with external cooling to give 8.5 g. 2,4-HO₂C(O₂N)C₆H₃SO₃K (XI). A suspension of 6.1 g. 2,5-H₂N(O₂N)C₆H₃Me in 20 cc. concentrated HCl was cooled to -5° and diazotized with 2.8 g. NaNO₂ in 10 cc. H₂O. The mixture was poured slowly with stirring into AcOH saturated with SO₂, and 2 g. CuCl₂.2H₂O dissolved in a min. amount of H₂O was added. The mixture was allowed to warm to 20°, stirred until gas evolution had ceased, and diluted with 240 cc. H₂O to precipitate 2,4-Me(O₂N)C₆H₃SO₂Cl (XII). XII was suspended in 60 cc. 5% KOH, heated to solution, treated with 120 cc. 10% KMnO₄, and heated until the color of KMnO₄ disappeared to give 3 g. XI. XI was converted to the acid chloride with PCl₅ in the usual manner. Dissolving X (R = H) in 100 cc. EtOH, adding a stoichiometric amount of EtONa in EtOH, and allowing the mixture to stand in ice several hrs. gave X (R = Na). This study involved multiple reactions and reactants, such as N-Benzyl-2-chloro-5-nitrobenzamide (cas: 83909-69-7Safety of N-Benzyl-2-chloro-5-nitrobenzamide).

N-Benzyl-2-chloro-5-nitrobenzamide (cas: 83909-69-7) 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.Safety of N-Benzyl-2-chloro-5-nitrobenzamide

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

Fungicidal properties of 2,2′-dicarbamido-4,4′-dinitrodiphenyl sulfides and of 5-nitro-1,2-benzoisothiazolones was written by Ponci, R;Baruffini, A.;Gialdi, F.. And the article was included in Farmaco, Edizione Scientifica in 1964.Application of 83909-69-7 The following contents are mentioned in the article:

The fungicidal activity was determined in vitro for several [2,3-XOC(O₂N)C₆H₃S]₂ (I) (X = H₂N, MeNH, BuNH, PhCH₂NH, PhNH, p-ClC₆H₄NH, 3-pyridyl-methylamino, morpholino) and II (R = H, Me, Bu, PhCH₂, Ph, p-ClC₆H₄, Ac, ClCH₂CO, EtCO, AmCO, Et₂CHCO, C₆H₁₅CO, PhCH₂CH₂OCO, Bz, p-ClC₆H₄CO, p-O₂ONC₆H4CO). All I and II exhibited high activity toward Candida albicans ATCC 10231 and Trichophyton mentagrophytes ATCC 8757; some of them were also tested against Aspergillus fumigatus, Cryptococcus neoformans, Madurella griesa, Microsporum audouini, Nocardia asteroides, and Sternphylium sarcinaeforme. The results confirm the antifungal activity of the substances tested and emphasize their wide spectrum of activity. Comparative tests with the I and II and the non-nitrated analogs demonstrated the influence of the NO₂ group on the activity. In the disulfide series the NO₂ group exerts a neg. effect in the case of the N-unsubstituted dicarbamide and a slight but neg. effect in the N-monosubstituted carbamides. The comparison of the II with the NO₂-free analogs showed a profound neg. effect by the NO₂ in the N-unsubstituted benzisothiazolone; however, slight variations of activity are observed in the N-substituted compounds 5-Nitro-1,2-benzoisothiazolone (III) pasted with an appropriate acid anhydride and heated 1-1.5 hrs. at 100-20° gave the corresponding II. III (10%) in H₂O stirred at 40° with the stoichiometric amount 2N NaOH, and the resulting Na salt dried 2 hrs. at 130°, suspended in dry C₆H₆ or MePh, treated with 1 mole 10% solution of a suitable halide in the same solvent, and refluxed 0.5-5 hrs. with stirring yielded the corresponding II. III (10%) in C₅H₅N treated dropwise at room temperature with stirring with 1 mole suitable halide, and heated 0.5 hr. at 50-60° gave the corresponding II. The appropriate amide (10-20%) in dry C₅H₅N treated at room temperature portionwise with 1 mole chlorobromide of 2,4-HO₂C(O₂N)C₆H₃SH in (CHCl₂)₂ and heated 1 hr. at 50-60° yielded the corresponding II. These methods gave II (R and m.p. given): Me, 190-2° (decomposition) (EtOH); ClCH₂, 165-7° (CHCl₃); Et, 179-80° [C₆H₆-petr. ether); Am, 108-9° (EtOH); Et₂OCH, 107° (MeOH); C₆H₁₃, 113° (EtOH); PhCH₂CH₂, 138-40° (EtOH); Ph, 180° (xylene); p-ClC₆H₄, 233-4° (MePh); p-O₂NC₆H₄, decomposition above 245° (xylene). This study involved multiple reactions and reactants, such as N-Benzyl-2-chloro-5-nitrobenzamide (cas: 83909-69-7Application of 83909-69-7).

N-Benzyl-2-chloro-5-nitrobenzamide (cas: 83909-69-7) 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 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 83909-69-7

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