Toluene → HCID 16751325, compound

HRID 2406705Notes

Reaction equation

HRID 2406705 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[CH:23]2>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH:24]=[CH:23]2

Participants

6

Reactant 3

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 871105-Chloroindole

Product 1

HCID 16751325HCID 16751325, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

p-Toluenesulfonyl chloride (2 g) and tetrabutyl ammonium hydrogen sulfate (250 mg) were added to a toluene (20 ml) solution containing 5-chloroindole (1.52 g), followed by stirring at room temperature for 11 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with water (×3) and saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=0:1 to 1:1), and a colorless solid of 5-chloro-1-tosyl-1H-indole (3.18 g) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with water (×3) and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=0:1 to 1:1)

Sources & evidence

ORD record
ord-62e3e3fbcf9a42c5b0f73883569e4b57
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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