Indole → Toluenesulfinyl chloride

HRID 1906933Notes

Reaction equation

HRID 1906933 reaction equation
[C:1]1([CH3:10])[C:2]([S:7]([O-])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[Na+].S(Cl)([Cl:14])=O.N1C2C(=CC=CC=2)C=C1.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]1([CH3:10])[C:2]([S:7]([Cl:14])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 23676349Sodium 2-methylbenzene-1-sulfinate

Product 1

HCID 13902623Toluenesulfinyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Toluenesulfinyl chloride was prepared according to Org. Syn., IV, 937 on half the scale described (that is, on 0.1 mole sodium toluenesulfinate). The crude sulfinyl chloride (15.2 g) was added dropwise to 11 g of indole dissolved in dichloromethane (200 ml) at 0° C. in the presence of 20 g of sodium bicarbonate. After 30 min at room temperature, the reaction mixture was washed well with saturated sodium bicarbonate solution, the phases separated and the organic phase dried and evaporated. The crude material was applied to a short silica gel column. Elution with dichloromethane removed a large amount of non-polar material. The product was removed with ethyl acetate. Upon recrystallization from ethyl acetate, the compound had melting point 120.5-121.5 (dec.) (corr.).

Workup

  1. washthe reaction mixture was washed well with saturated sodium bicarbonate solution
  2. customthe phases separated
  3. customthe organic phase dried
  4. customevaporated
  5. washElution with dichloromethane
  6. customremoved a large amount of non-polar material
  7. customThe product was removed with ethyl acetate
  8. customUpon recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-160f139d5c1e4de1875a2a8fcdf5ef50
Source dataset
uspto-grants-1987_03
Patent number
US04654360

Reaction notes

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