Methyl iodide → 3-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 840223

Reaction equation

HRID 840223 reaction equation
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].[C:8](=O)([O-])[O-].[K+].[K+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([N:24]=[C:25]=[S:26])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.CI>CC(C)=O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:24][C:25]([S:26][CH3:8])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75283(Methylsulfonyl)acetonitrileHCID 1454223,5-Dimethoxyphenyl isothiocyanate

Product 1

HCID 701502363-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrileYield 48.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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-dimethoxyphenyl isothiocyanate (0.96 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 23 h, then filtered and washed with ethanol. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 4 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 to give the title compound (0.728 g, 48%). 1H NMR (200 MHz, CDCl3): δ=2.27 (s, 3H), 3.19 (s, 3H), (s, 3H), 3.80 (s, 6H), 6.48 (t, 1H), 6.44 (d, 2H) EI SP/MS: 328 (M+).

Workup

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

Sources & evidence

ORD record
ord-5d27ecbf65814e65852f0893b374a07e
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Linked notes

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