Dimethyl Sulfoxide → 2-(Bis(methylsulfanyl)methylidene)propanedinitrile

Participants

Reaction Conditions

Reaction Steps

Add malononitrile (50.0 g, 757 mmol) to dry DMSO (600 mL), mechanically stir, cool to 15° C., and place under nitrogen. Add NaH (60%, 40 g, 1.00 mol) in small portions over 25 min keeping the internal temperature <25° C. and stir mixture. After 10 min, slowly add carbon disulfide (45.5 mL, 757 mmol) over 20 min at the same temperature. Stir at room temperature for 2.5 h then add additional NaH (60%, 29.6 g, 0.74 mol) while keeping the temperature constant with external cooling. Stir for 1.5 h at rt then cool to 15° C. Add iodomethane (103.7 mL, 1.67 mol) over 15 min. Stir resulting mixture overnight then pour into water (2.8 L). Stir the resulting dark orange precipitate for 15 min then collect by filtration, wash with water, partially air-dry, and wash with hexanes. Air-dry the tan powder to a constant weight (103 g) then recrystallize from 2-propanol. Filter solid, wash with cold 2-propanol and hexanes, then dry to afford the title compound: 1H NMR (DMSO-d6): δ 2.78 (s, 6H); 13C NMR (DMSO-d6): δ 186.0, 113.3, 74.2, 18.9.

Provenance & Evidence