27703-15-7

Upstream product

• 33842-02-3 dichloromethylenedimethyliminium chloride 
• 70-55-3 toluene-4-sulfonamide 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 34656-65-0 Dimethyltrichloromethylamine 

Downstream Products

• 13839-37-7 N-<(Dimethylamino)hydrazinomethylen>-p-toluolsulfonamid 
• 13750-34-0 N--p-toluolsulfonamid 
• 84274-88-4 N--p-toluolsulfonamid 
• 84274-95-3 1-1,N¹-Dimethyl-N²-(p-tosyl)amidino>-5--1,2,3-triazol 
• 80608-56-6 N₁,N₁-Dimethyl-3-(N-methylanilino)-N₂-tosylpropiolamidin 
• 71715-39-4 N-(toluene-4-sulfonyl)-morpholine-4-carboximidic acid dimethylamide 

Relevant academic research and scientific papers

Iminium Salts in Quantitative Gas/Solid and Solid/Solid Reactions

Iminium salts that are highly susceptible to hydrolysis are quantitatively prepared and reacted in the solid state without solvents or liquid phases. Atomic force microscopy AFM helps in elucidating the mechanism of these still unusual gas-solid and solid-solid syntheses by recording surface topographies of reacting crystals of L-histidine (10) and triphenylverdazyl (15). Various imines add gaseous HCl or HBr to form stable iminium halides (1, 3, 4, 5, 11) even if frozen liquids of very weak heterocyclic bases are treated at low temperatures. Another way for quantitative yields of iminium salt hydrates (6) starts with solid primary ammonium halides and gaseous acetone. o-Phenylenediamines (7) give quantitatively 1,5-benzodiazepines (9) by solid state cyclization of bis-iminium salt intermediates (8). Crystalline nitroxyls (12) and triphenylverdazyl (15) undergo stoichiometric one-electron transfer with gaseous NO2 or XeF2 to give nitrosonium (14) and azonium salts (17). The solid state chlorination of tetramethylthiuramdisulfide (18) or dimethylthiocarbamoylchloride (20) yields phosgene dimethyliminiumchloride (Viehe salt 21) in quantitative yield. Solid Viehe salt is quantitatively treated with gaseous Cl2 to give the trichloride 19 and solid SbCl5 or PCl5 to produce the hexachloroantimoniates (22), -phosphates (23). Solid brenzcatechol (24), mercaptobenzimidazole (27), p-nitroaniline (30), N-methylbenzothiazolone-2-hydrazone (34) and acetophenone (41) are treated with 21 to give the corresponding chloroiminium salts (25, 28, 31, 35, 43). p-Toluenesulfonamide (37) and 22 give the chloroiminium salt 38.These quantitative solid-solid reactions are most easily run in ball mills with cooling device. The "waste-free" techniques achieve exclusion of moisture in an elegant way. The preparative use of the versatile products with nucleophiles is indicated. The three-step solid-state mechanisms are discussed.

Synthesis and Reactivity of N',N'-Disubstituted N-arenesulfonamides

The synthesis of the amidino azides 3a-k mentioned in the title can be performed by direct chloride/azide exchange of the correspondingly substituted chlorides 1 or by nitrosation of the corresponding hydrazine derivatives 2.The azides 3 show no tendency, to isomerize to the valence tautomeric 5-amino-1-(arylsulfonyl)tetrazoles 4. - The azides 3 react with triphenylphosphane under nitrogen evolution to give the iminophosphoranes 5, while with methylene-active compounds the corresponding diazo compounds and the guanidines 6 are formed.The amidino azides add smoothly to the ynamines 7 to furnish the triazoles 8 which, depending on the substituents, isomerize partly or completely to yield the diazoamidines 9.