Toluene → HCID 16751325, compound

HRID 1620057Notes

Reaction equation

HRID 1620057 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-e54c7d3fbdc5439490280358cfe5738e
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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