Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1) → 3-[3-butyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a 8 mL vial was added 3-(3-butyl-4-oxothiazolidin-2-ylideneamino)benzonitrile (55 mg, 0.20 mmol), 3-methyl-2-(methylthio)benzothiazol-3-ium p-toluenesulfonate (73 mg, 0.20 mmol), anhydrous MeCN (2 mL) and TEA (70 μL, 0.50 mmol). The reaction mixture was first Warmed to 50° C. and the resulting solution was allowed to stir at room temperature for 16 h. The product mixture was concentrated under reduced pressure, chromatographed (silica gel, 1:99 MeOH/DCM) and then recrystallized from MeCN to give the title product (11.8 mg) as a yellow solid. 1H-NMR (CDCl3): δ 7.52 (1H, dd), 7.38-7.48 (2H, m), 7.32-7.37 (2H, m), 7.25 (1H, m), 7.18 (1H, m), 7.06 (1H, d), 3.96 (2H, t), 3.75 (3H, s), 1.77 (2H, m), 1.44 (2H, m), 0.98 (3H, t); MS(ESI): 421 (MH+).

Provenance & Evidence