Sodium Chloride → 3-(Methanesulfinyl)-1H-indole

HRID 1906932Notes

Reaction equation

HRID 1906932 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=[O:2].[K+].[K+].[CH3:13][S:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1.[Cl-].[Na+]>O.CO>[CH3:13][S:14]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:2]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 24412Potassium PersulfateHCID 108882523-methylsulfanyl-1H-indole

Product 1

HCID 130306043-(Methanesulfinyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Potassium persulfate (KHSO5, 55 g, 179 mmol) in water (300 ml) was slowly added to a solution of 3-methylthioindole (29.3 g, 179 mmol) in methanol (300 ml) cooled in a ice bath. One half hour after the addition was completed, water was added, the solution was saturated with sodium chloride and the product was extracted into chloroform. The extract was dried, evaporated in vacuo and the residue was crystallized from chloroform-ethyl acetate to give the title product.

Workup

  1. temperaturecooled in a ice bath
  2. additionOne half hour after the addition
  3. extractionthe product was extracted into chloroform
  4. customThe extract was dried
  5. customevaporated in vacuo
  6. customthe residue was crystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-ab3cf6f5e7554f3a9cf5917d310e0113
Source dataset
uspto-grants-1987_03
Patent number
US04654360

Reaction notes

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