587-14-4

Usage

InChI:InChI=1/C12H12N2O2S/c13-17(15,16)14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,13,15,16)

Upstream product

• 858798-56-8 formyl-phenyl-sulfamoyl chloride 
• 62-53-3 aniline 
• 63489-51-0 acetyl-phenyl-sulfamoyl chloride 
• 76167-37-8 N-(chlorosulfonyl)benzanilide 
• 13449-19-9 N-Phenylsulfamoylazid 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 106-50-3 1,4-phenylenediamine 
• 87708-16-5 N-phenyl-2-oxooxazolidine-3-sulfonamide 

Downstream Products

• 103-84-4 Acetanilid 
• 1752-96-1 N-phenylnicotinamide 
• 2364-50-3 isovaleranilide 
• 621-06-7 2,N-diphenylacetamide 
• 864131-95-3 N,N'-diphenylformamidine 
• 6832-96-8 2-ethyl-N-phenylbutanamide 
• 71764-61-9 N,N'N-Trisphenyl-1,3,5-benzenetricarbonamide 
• 95196-99-9 N,N’-bis(4-bromophenyl)sulfamide 
• 620-81-5 N,N'-Diphenyloxamid 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 6832-98-0 palmitanilide 
• 637-54-7 N-phenylstearamide 
• 93-98-1 N-phenyl benzoyl amide 
• 6833-13-2 2-chlorobenzanilide 

Relevant academic research and scientific papers

Electrochemical synthesis of sulfamides

Herein we demonstrate the first electrochemical synthesis protocol of symmetrical sulfamides directly from anilines and SO2mediated by iodide. Sulfamides are an emerging functional group in drug design. Highlights are the direct use of SO2from a stock solution and no necessity of any supporting electrolyte. Overall, the reaction has been demonstrated for 15 examples with yields up to 93%.

Ultrasonic assisted green protocol for the synthesis of sulfamides

An improved environmentally benign method for synthesis of sulfamides under focused ultrasound irradiation and under solvent-free and catalyst-free conditions has been carried out by the reaction of amines or amino esters with sulfuryl chloride. This approach allows the synthesis of products in excellent yields and in short reaction time.

Vicinal Diamination of Arenes with Domino Aryne Precursors

Vicinal diamination of domino aryne precursors was achieved with sulfamides. The reaction proceeds through a two-aryne pathway, accepting two N-nucleophiles at the 1,2-positions of an arene ring. Symmetrical and unsymmetrical diaminobenzenes were readily obtained.

Microwave-assisted synthesis of some substituted sulfamides

Microwave-assisted synthesis of some substituted open-chain and cyclic sulfamides, by amine-exchange reaction, was studied in a modified domestic microwave oven. Reaction times and yields under microwave radiation were compared with classical heating. Synthesis of the sulfamides under microwave irradiation gave better yields with the desired compounds, and in considerably reduced reaction times, than those obtained by classical heating. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures.]

Investigation of the acid-catalyzed hydrolysis and reaction mechanisms of N,N′-diarylsulfamides using various criteria

The mechanism of acid-catalyzed hydrolysis of a series of p-substituted N,N′-diarylsulfamides was investigated in aqueous mineral acid solutions. Rate profiles, reaction activation parameters, catalytic order of strong acids, solvent isotope effects, and analysis of the kinetic data by the excess acidity method suggest a change in the mechanism from A2 to A1. While the hydrolysis proceeds with an A2 mechanism in low acidity regions, an A1 mechanism takes place in high acid concentrations. Copyright

Copper-catalyzed oxidative amination and allylic amination of alkenes

Enamines and enamides are useful synthetic intermediates and common components of bioactive compounds. A new protocol for their direct synthesis by a net alkene C-H amination and allylic amination by using catalytic Cu II in the presence of MnO2 is reported. Reactions between N-aryl sulfonamides and vinyl arenes furnish enamides, allylic amines, indoles, benzothiazine dioxides, and dibenzazepines directly and efficiently. Control experiments further showed that MnO2 alone can promote the reaction in the absence of a copper salt, albeit with lower efficiency. Mechanistic probes support the involvement of nitrogen-radical intermediates. This method is ideal for the synthesis of enamides from 1,1-disubstituted vinyl arenes, which are uncommon substrates in existing oxidative amination protocols. A new protocol for the direct synthesis of enamides and allylic amines by oxidative N-H/C-H coupling of N-sulfonylanilines with vinylarenes is presented. The reaction works in both inter- and intramolecular modes and is catalyzed by copper salts by using MnO2 as the stoichiometric oxidant (see scheme). Nitrogen heterocycles including indoles, benzothiazine dioxides, and dibenzazepines can be formed. Copyright

Dinuclear titanium complexes with sulfamide ligands as precatalysts for hydroaminoalkylation and hydroamination reactions

A new dinuclear titanium sulfamide complex was synthesized from N,N-diphenylsulfamide and Ti(NMe2)4 and used as a precatalyst for the intermolecular hydroaminoalkylation of alkenes as well as the intramolecular hydroamination of alke

DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.

Sulfamides and sulfamide polymers directly from sulfur dioxide

SO2 gas is effectively used for the preparation of N,N′-diarylsulfamides and shape-persistent sulfamide polymers, which utilize a network of intermolecular N-H...O=S hydrogen bonds to self-assemble into soft porous materials. The Royal Society of Chemistry 2006.

Sulfamide synthesis via Pd-catalysed cross-coupling

A novel efficient procedure for the improved synthesis of aryl-substituted sulfamides via a Pd-catalysed arylation of sulfamide is reported.