Preparation of N-(Substituted formyl) dialkylamino(thioxo)methanesulfenamides

Article abstract of DOI:10.1246/bcsj.64.3732

N-(Substituted formyl)dialkylamino(thioxo)methanesulfenamides (R2NCSSNHCOR', 2), anti-foggants for silver halide photographic materials as well as potential precursors for 1,4,2-dithiazolium salts, were prepared in good yields in two ''one-pot'' procedures.Various amide-type compounds (R'CONH2, 1) were treated successively with NaH and I2 and then condensed with dialkylditiocarbamates (Method A); or 1 were reacted with tetraalkylthiuram disulfides after treatment with NaH (Method B).These methods allowed a wide variation of substituents R' in 2: R' = H, dialkylamino, alkoxy, aryl, alkyl, and heterocyclic substituent.