Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-3-indolecarboxaldehyde

HRID 572467Notes

Reaction equation

HRID 572467 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[OH-].[K+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([S:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH:10]=[O:11])=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 10256Indole-3-CarboxaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 3633341-(Phenylsulfonyl)-3-indolecarboxaldehydeYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of indole 3-carboxaldehyde (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stirred until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stirred for half hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33%. 1H NMR (500 MHz, CDCl3) δ 10.17 (s, 1H), 8.25-8.39 (m, 2H), 7.97-8.09 (m, 3H), 7.69 (t, J=7.33 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.39-7.54 (m, 2H). MS (ESI) calcd for C15H11NO3S 285.1. found 286.0 [M+H]+.

Workup

  1. customThe ethanol was completely removed in vacuum
  2. dissolutionthe residual was dissolved in acetone (250 mL)
  3. stirringThe reaction mixture was stirred for half hour
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated
  6. customrecrystallized from methanol
  7. customto give a white solid

Sources & evidence

ORD record
ord-ff0ad039141445f5a0b63a9f401aae55
Source dataset
uspto-grants-2015_05
Patent number
US09029408B2

Reaction notes

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