Benzenesulfonyl chloride → 1H-Indole, 5-nitro-1-(phenylsulfonyl)-

HRID 84199

Reaction equation

HRID 84199 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[OH-].[K+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:15]1([S:21]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 225235-Nitroindole

Product 1

HCID 121633031H-Indole, 5-nitro-1-(phenylsulfonyl)-Yield 92.2%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

After a suspension of 5-nitroindole (25) (1.00 g, 6.17 mmol), tetrabutylammonium bisulfate (0.32 g, 0.93 mmol) and KOH (0.69 g, 12.33 mmol) in CH2Cl2 (20 mL) was stirred for 30 min, benzenesulfonyl chloride (1.18 ml, 9.25 mmol) was added and stirred at room temperature overnight. The reaction was quenched with water extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:4) to afford 26 (1.72 g). 1H NMR (500 MHz, CD3OD): δ 6.81 (d, J=3.6 Hz, 1H), 7.48-7.51 (m, 2H), 7.58-7.61 (m, 1H), 7.73 (d, J=3.69 Hz, 1H), 7.90 (d, J=7.64 Hz, 2H), 8.09 (d, J=9.0 Hz, 1H), 8.21 (dd, J=9.0, 2.0 Hz, 1H), 8.47 (d, J=2.0 Hz, 1H).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with CH2Cl2 (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:4)

Sources & evidence

ORD record
ord-9f906ee874db41029ec8559537c63833
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Linked notes

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