5033-23-8

Usage

InChI:InChI=1/C11H15NO2S/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8H,2,5-6,9-10H2

Upstream product

• 110-89-4 piperidine 
• 98-09-9 benzenesulfonyl chloride 
• 4106-18-7 1-(phenylsulfonyl)-1H-benzo[d][1,2,3]triazole 
• 873-55-2 sodium benzenesulfonate 
• 2156-71-0 N-chloropiperidine 
• 7744-25-4 1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 
• 155164-57-1 2-benzenesulfonyl-4,5-dichloropyridazin-3-one 
• 35856-62-3 1-piperidinesulfonyl chloride 
• 71-43-2 benzene 
• 970-88-7 2,4-dinitrophenyl benzenesulfonate 
• 108-86-1 bromobenzene 
• 3313-84-6 4-nitrophenyl benzenesulfonate 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 106762-74-7 diphenyl<2-(piperidinosulfonyl)phenyl>methanol 
• 110-89-4 piperidine 
• 98-09-9 benzenesulfonyl chloride 
• 46855-40-7 5-(benzenesulfonyl-methyl-amino)-valeric acid 
• 133932-29-3 5-benzenesulfonylamino-valeric acid 

Relevant academic research and scientific papers

An efficient protocol for the selective reduction of benzenesulfonyllactam to benzenesulfonyl cyclic amine

The selective reduction of N-benzenesulfonylpiperidin-2-one to N-benzenesulfonylpiperidine was accomplished through the use of NaBH4 with either ZrCl4 or SnCl4 and by silane-mediated two-step reductions.

Synthesis of Sulfones and Sulfonyl Derivatives using Sodium (tert-butyldimethylsilyl)oxymethanesulfinate

The present invention relates to a method for manufacturing a sulfone and sulfonyl derivative compound using sodium (tert-butyldimethylsilyl)oxymethanesulfinate, which is a novel organic sulfin salt, wherein the novel organic sulfin salt has good stability, environmental friendliness and economy, and is easy to handle, and thus significantly reduces the amount of transition metal catalysts and the amount of organic sulfin salts used when introducing aryl or alkenyl. Also, alkylation, arylation, amination, and fluorination are all possible during secondary functionalization. Therefore, the present invention can be usefully used in preparation and mass production of various kinds of sulfones and derivatives thereof including asymmetric sulfone derivatives.

AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST

The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.

Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones

We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition-elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S -alkylation to produce sulfones in high yields. In the presence of N -bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.

Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand

A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Hypervalent Iodine Mediated Sulfonamide Synthesis

A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.

Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines

An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism.

PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes

A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.