19377-04-9

Usage

InChI:InChI=1/C13H12ClNO2S/c1-10-5-7-13(8-6-10)18(16,17)15-12-4-2-3-11(14)9-12/h2-9,15H,1H3

Upstream product

• 108-42-9 3-chloro-aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 625-99-0 3-iodochlorobenzene 
• 70-55-3 toluene-4-sulfonamide 
• 941-55-9 4-toluenesulfonyl azide 
• 777898-07-4 2-chloro-6-[(4-methylphenyl)sulfonamido]benzoic acid 
• 121-73-3 3-Nitrochlorobenzene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 21849-40-1 dibromamine-T 
• 63503-60-6 3-chlorophenylboronic acid 
• 932-78-5 1-chloro-3-nitrosobenzene 
• 106-49-0 p-toluidine 
• 4083-64-1 Tosyl isocyanate 
• 127-65-1 chloroamine-T 

Downstream Products

• 60498-61-5 N-(3-chloro-4-nitrophenyl)-4-methylbenzenesulfonamide 
• 198839-44-0 N-(5-chloro-2-nitrophenyl)-4-methylbenzenesulfonamide 
• 735271-17-7 N-(5-trimethylsiloxy-5,5-diphenyl-3-pentynyl)-N-(p-toluenesulfonyl)-m-chloroaniline 
• 858005-32-0 toluene-4-sulfonic acid-(5-chloro-2,4-dinitro-anilide) 
• 1097201-82-5 N-(3-chlorophenyl)-4-nitro-N-tosylbenzamide 
• 1097201-77-8 N-(3-chlorophenyl)-N-tosylbenzamide 

Relevant academic research and scientific papers

Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans

A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance. (Figure presented.).

Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium

A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.

Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under Metal-Free Conditions?

A metal-free reaction of nitrosoarenes, aryldiazonium tetrafluoroborates, and sulfur dioxide under mild conditions is developed, giving rise to sulfonamides in moderate to good yields. This transformation proceeds efficiently at room temperature in the presence of cyclohexa-1,4-diene with a broad reaction scope. Good functional group compatibility is observed, including cyano, halo, and ester. A plausible mechanism involving a radical process with the insertion of sulfur dioxide is proposed, and cyclohexa-1,4-diene serves as the reductant during the transformation.

Facile Chan-Lam coupling using ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene

Ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of graphene followed by metallation with copper (I) iodide. The [GrFemImi]NHC@Cu complex has been characterized by fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), CP-MAS 13C NMR spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), energy dispersive X-ray (EDX) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET) surface area analysis and X-ray diffractometer (XRD) analysis. This novel complex served as a robust heterogeneous catalyst for the synthesis of bioactive N-aryl sulfonamides from variety of aryl boronic acids and sulfonyl azides in ethanol by Chan-Lam coupling. Recyclability experiments were executed successfully for six consecutive runs.

Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates

An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor

Differentiation of isomeric haloanilines by tosylation in combination with electrospray ionization mass spectrometry

Differentiation of the isomeric haloanilines still remains a challenging and?necessary?analytic task due to their identical retention time in chromatography and similar mass spectra. In this work, p-tosylation of haloanilines by reaction of haloanilines with p-toluenesulfonyl chloride resulted in the corresponding N-tosyl haloanilines. Fragmentation of protonated N-tosyl haloanilines in electrospray ionization tandem mass spectrometry (ESI-MS/MS) mainly resulted in tosyl cation, haloaniline radical cation, and halohydroxyaniline radical cation. The MS/MS of the three group isomeric derivatives showed significant difference in abundance distribution of these product ions, respectively. Theoretical calculations showed that the stability of the ion-neutral complex (INC) is a key factor influencing the relative intensity of the product ions. The three group isomeric derivatives were also separated by high performance liquid chromatograph (HPLC) at conventional conditions. p-Tosylation combined tandem MS (or HPLC) technique were carried out to realize the differentiation of isomeric haloanilines.

Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature

A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides

A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

CuI catalyzed sulfamidation of arylboronic acid using TsNBr2 at room temperature

An expeditious protocol for amidation arylboronic acid has been developed using TsNBr2 as the nitrogen source in presence of a CuI as catalyst. Various arylboronic acids could be transformed into corresponding N-arylsulfonamide derivatives within a very short time using CuI as catalyst in presence of DBU at room temperature.

Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources

One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.