Methyl iodide → 3-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 840243

Reaction equation

HRID 840243 reaction equation
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].[C:8](=O)([O-])[O-].[K+].[K+].[CH2:14]1[O:22][C:21]2[CH:20]=[CH:19][C:18]([N:23]=[C:24]=[S:25])=[CH:17][C:16]=2[O:15]1.CI>CC(C)=O>[O:22]1[C:21]2[CH:20]=[CH:19][C:18]([NH:23][C:24]([S:25][CH3:8])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])=[CH:17][C:16]=2[O:15][CH2:14]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75283(Methylsulfonyl)acetonitrileHCID 1235931,3-Benzodioxole, 5-isothiocyanato-

Product 1

HCID 701495853-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrileYield 65.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methanesulfonylacetonitrile (2.85 g, 23.9 mmol) in dry acetone (50 ml) was stirred while dry potassium carbonate (6.61 g, 47.8 mmol) and 3,4-methylenedioxyphenyl isothiocyanate (4.50 g, 25.1 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (4.43 ml, 71.8 mmol) was added to the filtrate, and stirring was continued for 4 h at 50° C. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 4.88 g (65%) of the title compound as golden brown crystals. Mp 168-170° C. 1H NMR (200 MHz, DMSO-d6): δ=2.30 (s, 3H), 3.33 (s, 3H), 6.06 (s, 2H), br s, 1H). (dd, 1H), 6.94 (d, 1H), 6.97 (d, 1H), 9.98 (br s, 1H).

Workup

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 4 h at 50° C
  5. customThe mixture was evaporated
  6. dissolutionthe residue was dissolved in dichloromethane
  7. extractionextracted with water and brine
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-87063392cd17478dbfe108883bca8cc8
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Linked notes

Loading…