4875-16-5Relevant academic research and scientific papers
Chlorosulfonation of some aldimine-isocyanate cycloadducts
Cremlyn, Richard J.,Ellam, Richard M.,Farouk, Sultan
, p. 1931 - 1941 (2007/10/03)
Attempts to chlorosulfonate 1,4-diphenyl-1,3-diazetidin-2-one (1) failed, but the 3-methyl derivative (2) reacted with chlorosulfonic acid to give the bis-sulfonyl chloride (3), characterized as the sulfonamides 4 and 5. 2,3,6-Triphenyl-2,3-dihydro-1,3,5-thiadiazin-4-one (6) with chlorosulfonic acid suffered an acid-catalyzed ring-opening reaction forming the sulfonyl derivatives (8, 9) of N-phenyl-N′-thiobenzoylurea (7). Condensation of 8 and 9 with diethylamine afforded the diethyl-sulfonamide (10). Dibenzylideneethylenediamine (11) reacted with thiobenzoyl isocyanate at room temperature to yield the cycloadduct 12; however at 90°C, N,N′-di (thiobenzoylcarbamoyl)ethylenediamine (13) was obtained. The cycloadduct 12 with chlorosulfonic acid gave the ring-opened disulfonyl chloride 14 and the diethylsulfonamide 15. 1,6-Diphenylhexahydro-s-triazine-2,4-dione (17) was converted into the dimethyl derivative (18), which with chlorosulfonic acid afforded the bis-sulfonyl chloride (19), characterized as the sulfonamides 20-22.
