1,2-Diaminocyclohexane (1.00 g, 8.76 mmol) was measured into a round bottomed flask (100 mL) and dichloromethane added (100 mL).  1,1’-Thiocarbonyldi-2(1H)-pyridone (4.40 g 18.94 mmol) was added slowly and the reaction was stirred overnight.  The solution was washed with water (200 mL) and the aqueous layer extracted with dichloromethane (100 mL).  The combined organic solution was then washed with brine (100 mL) and dried over MgSO₄.  The dichloromethane was evaporated under reduced pressure to leave a thick red oil with an orange solid.  Hexane : ethyl acetate (2:1, 5 mL) was then added and the mixture was gently heated to allow the product the dissolve. A sparingly soluble orange solid remained. The solution was then eluted through a silica column with hexane : ethyl acetate (2:1).  The appropriate fractions were combined to give an off white low melting point solid (yield 0.810 g, 47 %).

¹H NMR (293 K, d₁-chloroform) d 1.33 (m, 2H, CH₂), 1.57 (m, 2H, CH₂), 1.72 (m, 2H, CH₂), 2.13 (m, 2H, CH₂), 3.67 (m, 2H, CH).

¹³C{¹H} NMR (293 K d₁-chloroform) d 22.9 (CH₂), 31.5 (CH₂), 60.0 (CH), 134.9 (Cq).

IR (nujol, cm^-1): 2946, 2863, 2362, 2341, 2046, 1448, 1363, 1347, 1305, 956, 721, 669.

Anal. Calcd. for C₈H₁₀N₂S₂: C, 48.45; H, 5.08; N, 14.13.  Found: C, 48.59; H, 4.95; N, 13.92.

MS (EI) m/z 198 (M⁺)

E. J. Crust, I. J. Munslow and P. Scott, Journal of Organometallic Chemistry, 2005, 690, 3373-3382.http://dx.doi.org/10.1016/j.jorganchem.2005.04.019