57186-68-2

Upstream product

• 75-03-6 ethyl iodide 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 5228-66-0 N-Methyl-N--formamid-diaethylacetal 
• 74-96-4 ethyl bromide 
• 16181-39-8 O-ethyl N-methyl toluene-4-sulphonimidate 
• 80-39-7 N-ethyl-4-methyl-benzenesulfonamide 
• 74-88-4 methyl iodide 
• 16697-83-9 N-methyl-N-tosylacetamide 
• 7677-24-9 trimethylsilyl cyanide 
• 624-78-2 N-Ethylmethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 4788-37-8 N-ethyl-N-methylbenzylamine 
• 141-78-6 ethyl acetate 
• 70-55-3 toluene-4-sulfonamide 

Relevant academic research and scientific papers

Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light

An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.

Eosin Y-Sensitized Photocatalytic Reaction of Tertiary Aliphatic Amines with Arenesulfonyl Chlorides under Visible-Light Irradiation

A mild, practical, and environmentally friendly route to vinyl sulfones and sulfonamides has been developed based on the reaction of aliphatic amines with arenesulfonyl chlorides in the presence of eosin Y as a photocatalyst under visible light. The method permits the selective formation of vinyl sulfones or sulfonamides, depending on the oxidation environment and solvent. A wide range of products were obtained in moderate to good yields under the optimized conditions.

The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation

The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).

Indium triiodide catalyzed reductive functionalization of amides via the single-stage treatment of hydrosilanes and organosilicon nucleophiles

The indium triiodide catalyzed single-stage cascade reaction of N-sulfonyl amides with hydrosilanes and two types of organosilicon nucleophiles such as silyl cyanide and silyl enolates selectively promoted deoxygenative functionalization to give α-cyanoamines and β-aminocarbonyl compounds, respectively.

NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst

Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright

Pseudomolecular Rearrangement of O-Ethyl N-Methyl Toluene-4-sulphonimidate to N-Ethyl-N-methyltoluene-4-sulphonamide and its Relevance to the Nucleophilic Properties of Neutral Sulphonamides

Kinetic studies are reported for the pseudo-molecular rearrangement of O-ethyl N-methyl toluene-4-sulphonimidate to N-ethyl-N-methyltoluene-4-sulphonamide in organic solvents at 34-100 deg C.Without catalysts, the rearrangement follows the equation rate = krearr 2, which is indicative of an intermolecular SN2 transalkylation via an ion-pair intermediate: it is accompained by concurrent E2 elimination to N-methyltoluene-4-sulphonamide.The rearrangement is catalysed by electrophilic reagents such as alkyl halides, ZnI2, and HBr where rate = k2 .For alkyl halides, a two-step mechanism via an ionic intermediate applies in which formation of the intermediate by an SN2 reaction between the substrate and alkyl halide is rate limiting.Other catalysts effect rearrangement by forming alkyl halides in an initial rapid reaction with the substrate.The results are discussed in relation to the ambident nucleophilic properties of sulphonamides.It is suggested that, like carboxylic acid amides and phosphinylamides, alkylation occurs most readily at the O-atom of neutral sulphonamides to give a sulphonimidate (kinetic product), which then rearranges in the presence of electrophilic catalysts to give an N-substituted sulphonamide (thermodynamic product).Rearrangement is normally too fast for the isolation of O-alkyl sulphonimidates, but O-aryl analogues can be obtained.