Bis(N,N-dibutylthiocarbamoyl) Disulfide

This experiment is performed according to literature method [1-3]. N,N-Dibutylamine 1 (20 mL, 0.024 mol) in ethanol solution and triethylamine (6.65 g, 0.048 mol) were cooled to 5°C under stirring. Then carbon disulfide (3.65 g. 0.48 mol) was added to the solution. After 1 hour of stirring, solid iodine (2,8 g, 0.022 mol) was added in portions and stirred until the colour disappeared completely. Then a methanolic solution of iodine was added dropwise until a faint colour persists. Excess of iodine was neutralised with Na₂S₂O₃ solution. The product was extracted with diethyl ether, washed thrice with water, dried over Na₂SO₄, filtered, and diethylether was evaporated at room temperature to give liquid compound 2. Yield: 83%

H¹ NMR (CCl₄) d (ppm): 1,00 (t, 12H, CH_3-); 1,48 (m, 16H, -CH₂-CH₂-); 2,73 (s, 8H, N-CH₂).

¹³C NMR (CDCl₃) d (ppm): 193 (-C=S), 55 (N-CH₂), 20 (CH₃).

IR (KBr , cm^-1) : 3000 (-S-S-); 1100 (C=S).

MS (m/z): 408 [M]⁺.

U.V : l max = 280 nm (-C=S).