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

HRID 63236

Reaktionsgleichung

Reaktionsgleichung von HRID 63236
[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

Komponenten

5

Edukt 4

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

Produkt 1

HCID 177503871-(benzenesulfonyl)-1H-indole-5-carbaldehydeAusbeute 32,6 %

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-95487d6359a04dfe9aebb7ce954924bf
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447049B2

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