D'Amico, Tung, and Dahlto slightly gray powdery solid had formed. The mixture was stirred for a further 30 min and filtered. The solid was dried in vacuo in a desiccator (CaClZ), yield 95-99%. Infrared spectra indicated the absence of the N-H group. N-Alkyl-N-p-toluenesulfonyl-2,4,6-trinitrobenzenesulfenamides. A solution of 3.5mmol of 2,4,6-trinitrobenzenesulfenyl chloride in 10 ml of benzene was added to a magnetically stirred suspension of 4 mmol of a silver ialt of N-alkyl-p-toluenesulfonamide in 30 ml of benzene and the mixture was stirred a t room temperature for 48 h. After filtration of the solid, the solution was evaporated and the residue chromatographed on silica gel with benzene-hexane (2:l) as an eluent. The products were purified by recrystallization from tetrahydrofuran-hexane (Table 11). ; N H R~R z (R1 = CHMez; Rz = CHZPh), 102-97-6; NHRlRz (RI = CHMe2; RZ = CHMeZ), 108-18-9; NHR1Rz (R1 = CHZPh; RZ = 2,4,6-Me&Hz), 60882-91-9; p-MeCeHdSOZNHR (R = CHZPh).Ag, 60882-92-0; p-MeCsH4SOzNHR (R = CHZMe&Ag, 60882-93-1; p-MeCeHdSOZNHR (R = CHMePhbAg, 60882-94-2; p-MeCeH4-SOzNHR (R = CMezCHzOMe).Ag, 60882-95-3; benzenesulfenyl chloride, 931-59-0; benzyl 2,4,6-trinitrobenzenesulfenate, 60882-96-4; benzyl alcohol, 100-51-6.Depending on reaction temperatures the reaction of potassium 2-mercaptobenzimidazole with 4-chloro-3,5-dinitrobenzotrifluoride afforded either the expected 2-(2,6-dinitro-4-trifluoromethylphenylthio) benzimidazole (3) or the unexpected 4-nitrobenzimidazo[2,l-b]benzothiazole ( 5 ) . Possible mechanism and supporting NMR, IR, and mass spectral data are discussed.