(5-Chloro-3-methylsulfanyl-indol-1-yl)-acetonitrile → (5-Chloro-3-methanesulfinyl-indol-1-yl)-acetonitrile

HRID 23399Notes

Reaction equation

HRID 23399 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]#[N:13])[CH:6]=[C:5]2[S:14][CH3:15].[OH:16]OS([O-])=O.[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]#[N:13])[CH:6]=[C:5]2[S:14]([CH3:15])=[O:16]

Participants

5

Reactant 2

HCID 22573959(5-Chloro-3-methylsulfanyl-indol-1-yl)-acetonitrileHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22574044(5-Chloro-3-methanesulfinyl-indol-1-yl)-acetonitrileYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5-chloro-3-methylsulfanyl-indol-1-yl)-acetonitrile (1.0 g, 4.22 mmole) dissolved in methanol (65 ml) cooled to ca. 0° C., was added a cold solution (ca. 7° C.) of Oxone® (1.29 g, 2.11 mmole) dissolved in water (40 ml) in portions over a 10 minute time period. The cooling bath was removed and the solution was stirred at room temperature for 4 h. Tlc analysis at this point showed some unreacted starting material and thus 0.1 g more Oxone® was added and the mixture continued stirring overnight. The reaction mixture was evaporated to dryness and the residue was taken up in methanol and the insoluble material was filtered. The methanol soluble material was isolated by evaporation of the solvent and the residue was triturated with ether which was discarded and then with toluene. The solid which remained was further purified by column chromatography (silica gel) eluting with methanol:methylene chloride (3:97). The resulting (5-chloro-3-methanesulfinyl-indol-1-yl)-acetonitrile weighed 0.851 g (80% yield) after drying.

Workup

  1. customThe cooling bath was removed
  2. additionwas added
  3. stirringthe mixture continued stirring overnight
  4. customThe reaction mixture was evaporated to dryness
  5. filtrationthe insoluble material was filtered
  6. customThe methanol soluble material was isolated by evaporation of the solvent
  7. customthe residue was triturated with ether which
  8. customThe solid which remained was further purified by column chromatography (silica gel)
  9. washeluting with methanol:methylene chloride (3:97)
  10. customafter drying

Sources & evidence

ORD record
ord-214593419bbd4481921c2e6fa9b26fea
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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