Methyl iodide → 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

To a solution of methanesulfonylacetonitrile (0.55 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,5-bis(trifluoromethyl)phenyl isothiocyanate (1,32 g, 4.7 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried (sodium sulfate) and concentrated. The residue was recrystallised from ethyl acetate/heptane 1:2 to give the title compound (1.55 g, 83%). Mp 129-131° C. 1H NMR (200 MHz, CDCl3): δ=2.35 (s, 3H), 3.25 (s, 3H), 7.77 (s, 2H), 7.80 (s, 1H)H), 9.90 (br s, 1H); EI SP/MS: 404 (M+).

1. filtrationfiltered
2. stirringThe mixture was stirred at room temperature for 2 h
3. filtrationThe reaction mixture was filtered
4. concentrationthe filtrate was concentrated
5. dissolutionThe residue was dissolved in dichloromethane
6. washwashed with water
7. dry with materialThe organic layer was dried (sodium sulfate)
8. concentrationconcentrated
9. customThe residue was recrystallised from ethyl acetate/heptane 1:2

ORD record

ord-a5adb4c5eb6b4c8486c0ee56cbd5c63b

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362205B1