Ethanol → 1-(benzenesulfonyl)-1H-indole-5-carbaldehyde

HRID 70063Notes

Reaction equation

HRID 70063 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](C=O)=[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.[CH2:24]([OH:26])C>>[C:14]1([S:20]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:24]=[O:26])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 7369Benzenesulfonyl chlorideHCID 10256Indole-3-CarboxaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 177503871-(benzenesulfonyl)-1H-indole-5-carbaldehydeYield 32.6%

Procedure

To a solution of indole-3-carboxaldehyde (100 mmol) in ethanol (500 mL) at room temperature was added potassium hydroxide (110 equiv), the mixture was stirred until total solubilization. The ethanol was completely removed in vacuum and acetone (250 mL) added followed by benzenesulfonyl chloride (110 equiv). The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 32.6% 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 and acetone (250 mL)
  2. additionadded
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customrecrystallized from methanol
  6. customto give a white solid

Sources & evidence

ORD record
ord-a3360716aa4249c49cbc435bd70f1f00
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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