Benzenesulfonyl chloride → HCID 89816088, compound

HRID 1482956Notes

Reaction equation

HRID 1482956 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[OH-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.ClCCl>[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 198489176-(Methylsulfanyl)-1H-indole

Product 1

HCID 89816088HCID 89816088, compoundYield 59.18%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(methylthio)-1H-indole (1 g, 6.13 mmol), NaOH (4.90 g, 122.6 mmol) and Bu4NHSO4 (207.8 mg, 0.613 mmol) in dichloromethane (20 mL) was added benzenesulfonyl chloride (1.29 g, 7.36 mmol). The reaction mixture was stirred at rt overnight. The mixture was quenched with water (30 mL) and extracted with dichloromethane (30 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography on silica gel eluted with PE/EtOAc 10:1 to afford 6-(methylthio)-1-(phenylsulfonyl)-1H-indole (1.1 g, 59.18% yield) as a white solid. LC-MS MS (ESI) m/z 304.0 [M+H]+. 1H NMR (CDCl3 400 MHz): δ 7.93-7.75 (m, 3H), 7.58-7.41 (m, 5H), 7.17 (dd, J1=8.0 Hz, J2=1.6 Hz, 1H), 6.63-6.60 (m, 1H), 2.53 (s, 3H).

Workup

  1. customThe mixture was quenched with water (30 mL)
  2. extractionextracted with dichloromethane (30 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel
  7. washeluted with PE/EtOAc 10:1

Sources & evidence

ORD record
ord-c7f6422b9fc64b3d8b70c1f78f239b62
Source dataset
uspto-grants-2016_08
Patent number
US09416135B2

Reaction notes

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