Benzenesulfonyl chloride → 5-(Phenylmethoxy)-1-phenylsulfonylindole

HRID 2423124Notes

Reaction equation

HRID 2423124 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 7369Benzenesulfonyl chloride2×HCID 146245-BenzyloxyindoleHCID 14798Sodium Hydroxide

Product 1

HCID 118246245-(Phenylmethoxy)-1-phenylsulfonylindoleYield 45.9%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4 M NaOH (100 mL, 0.4 mol) was added to a solution of 5-benzyloxyindole (20 g, 0.09 mol), tetrabutylammonium hydrogen sulfate (6.1 g, 0.018 mol) and benzenesulfonyl chloride (27 g, 0.15 mol) in DCM (500 mL) The mixture was stirred at room temperature for 6 hours and additional benzenesulfonyl chloride (4.1 g, 0.023 mol) was added. The mixture was stirred overnight and diluted with water and DCM. The mixture was transferred to a separation funnel and extracted with DCM (2×), dried (MgSO4) and evaporated. The crude product was suspended in diethylether (1000 mL) and filtered. The solid cake was washed with diethylether (2×) and discarded. The filtrate was evaporated to approximate 100 mL (precipitation of white solid) and filtered. The white crystals were washed with cold diethylether (2×) and dried in vacuo to give 15 g of a white solid. MS m/z 364 [M+H]+

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe mixture was transferred to a separation funnel
  3. extractionextracted with DCM (2×)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. filtrationfiltered
  7. washThe solid cake was washed with diethylether (2×)
  8. customThe filtrate was evaporated to approximate 100 mL (precipitation of white solid)
  9. filtrationfiltered
  10. washThe white crystals were washed with cold diethylether (2×)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-0b3b9d9d5434468e8d9252765466e64a
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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