Melatonin → HCID 11090036, Verbindung

HRID 382324

Reaktionsgleichung

Reaktionsgleichung von HRID 382324
[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].[OH-].[Na+].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][O:16][C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[N:9]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[CH:8]=[C:7]2[CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1]

Komponenten

6

Edukt 3

HCID 896MelatoninHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 11090036HCID 11090036, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5 g of melatonin are dissolved in 150 ml of dichloromethane, and then 3.41 g of sodium hydroxide and 0.35 g of tetrabutylammonium hydrogen sulphate are added. The reaction mixture is then cooled in an ice-bath, and 4.06 ml of benzenesulphonyl chloride are added dropwise. After stirring overnight at room temperature, the excess sodium hydroxide and the catalyst are filtered off, the solvent is removed by evaporation in vacuo, and the resulting solid is recrystallised to yield the title product in the form of white crystals.

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled in an ice-bath
  2. filtrationthe excess sodium hydroxide and the catalyst are filtered off
  3. customthe solvent is removed by evaporation in vacuo
  4. customthe resulting solid is recrystallised

Quellen und Nachweise

ORD-Eintrag
ord-772d898a01774a5f803c6fe47044ad3a
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310074B1

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