Methyl iodide → 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 840212

Reaction equation

HRID 840212 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([N:30]=[C:31]=[S:32])[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.CI>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:31]([NH:30][C:24]2[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:22]([O:21][CH3:20])[CH:23]=2)[S:32][CH3:14])[C:12]#[N:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1454223,5-Dimethoxyphenyl isothiocyanateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

Product 1

HCID 701503682-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrileYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 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 2 h 15 min and then filtered. 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 concentrated. The residue was dissolved in DCM, washed with water, dried (Na2SO4) and concentrated. The residue was crystallised from ethyl acetate/heptane 1:2 to give 1.27 g (65%) of the title compound. Mp 119.5-123° C.; 1H NMR (200 MHz, CDCl3): δ=2.29 (s, 3H), 3.80 (s, 6H), 3.36 (m, 3H), 7.53 (d, 2H), 7.87 (d, 2H), 9.82 (br s, 1H); EI SP/MS: 424 (M+).

Workup

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 4 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was crystallised from ethyl acetate/heptane 1:2

Sources & evidence

ORD record
ord-781fcfd5ea5945398c9d554b3fdb04e0
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Linked notes

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