4-Toluenesulfonyl chloride → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde

HRID 565411

Reaktionsgleichung

Reaktionsgleichung von HRID 565411
[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.[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>C(N(CC)CC)C>[S:12]([N: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)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 10256Indole-3-Carboxaldehyde

Produkt 1

HCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a 25 mL round bottom flask containing a solution of crude indole-3-carboxaldehyde (4.5 mmol) in 10 mL of triethylamine was added 1.3 g (6.7 mmol) of tosyl chloride. The reaction mixture was heated to 95° C. for 4 h. The reaction mixture was quenched by pouring into 10 mL of ice water and filtered. The solid was washed with water (3×10 mL), triterated with ether (25 mL), and dried in vacuo to give N-tosyl-indole-3-carboxaldehyde (85-90% yield).

Aufarbeitung

  1. customThe reaction mixture was quenched
  2. additionby pouring into 10 mL of ice water
  3. filtrationfiltered
  4. washThe solid was washed with water (3×10 mL), triterated with ether (25 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-57a794a6f41442d4bfd300e90dc784e7
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172084B2

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