Acetone → 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 279128Notes

Reaction equation

HRID 279128 reaction equation
C([S:4]([CH2:7][C:8]#[N:9])(=[O:6])=[O:5])CC.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]([F:32])([F:31])[C:18]1[CH:19]=[C:20]([N:28]=[C:29]=[S:30])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1.[CH3:33]I.[CH3:35][C:36]([CH3:38])=O>>[F:25][C:24]([F:26])([F:27])[C:22]1[CH:21]=[C:20]([NH:28][C:29]([S:30][CH3:33])=[C:7]([S:4]([CH:36]([CH3:38])[CH3:35])(=[O:6])=[O:5])[C:8]#[N:9])[CH:19]=[C:18]([C:17]([F:31])([F:16])[F:32])[CH:23]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5194412-(Propane-1-sulfonyl)acetonitrileHCID 27333953,5-Bis(trifluoromethyl)phenyl isothiocyanate

Product 1

HCID 865837393-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrileYield 99%

Procedure

A solution of 2-propanesulphonylacetonitrile (4.0 g, 27.2 mmol) in dry acetone (50 ml) was stirred while dry potassium carbonate (7.52 g, 54.4 mmol) and 3,5-bis(trifluoromethyl)phenyl isothiocyanate (7.72 g, 4.87 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 (5.08 ml, 81.6 mmol) was added to the filtrate, and stirring was continued for 48 h. 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 11.65 g (99%) of the title compound as yellowish brown crystals. Mp 130-133° C.1H NMR (200 MHz, CDCl3): δ=1.47 (d, 6H), 2.35 (s, 3H), 3.44 (heptet, 1H), 7.73 (s, 2H), 7.80 (s, 1H), 10.10 (br s, 1H);

Workup

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 48 h
  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-5eebe8b707cb4261be0e869ad8d31568
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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