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

Temperature

15 °C

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.

1. stirringthe internal temperature <25° C. and stir mixture
2. stirringStir at room temperature for 2.5 h
3. stirringStir for 1.5 h at rt
4. temperaturethen cool to 15° C
5. stirringStir
6. customresulting mixture overnight
7. stirringStir the resulting dark orange precipitate for 15 min
8. filtrationthen collect by filtration
9. washwash with water
10. custompartially air-dry
11. washwash with hexanes
12. customAir-dry the tan powder to a constant weight (103 g)
13. customthen recrystallize from 2-propanol
14. filtrationFilter solid
15. washwash with cold 2-propanol and hexanes
16. customdry

ORD record

ord-78e1b4895bd548fea1f0c08d02f3beb6

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642361B2