Melatonin → HCID 11090036, Verbindung

HRID 429776

Reaktionsgleichung

Reaktionsgleichung von HRID 429776
[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

Dissolve 5 g (21.5 mmol) of melatonin in 150 ml of dichloromethane. With stirring, add 3.41 g (84 mmol) of sodium hydroxide and 0.35 g (0.9 mmol) of tetrabutylammonium hydrogen sulphate. Cool the mixture in an ice-bath, and add 4.06 ml (31.5 mmol) of benzenesulphonyl chloride dropwise. After stirring overnight at room temperature, filter off the excess sodium hydroxide and the catalyst. Remove the solvent by evaporation in vacuo, and recrystallise the resulting solid.

Aufarbeitung

  1. temperatureCool the mixture in an ice-bath
  2. stirringAfter stirring overnight at room temperature
  3. filtrationfilter off the excess sodium hydroxide
  4. customRemove the solvent
  5. customby evaporation in vacuo
  6. customrecrystallise the resulting solid

Quellen und Nachweise

ORD-Eintrag
ord-4c711e232afa482e9afbc1e43a0ec931
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06319930B1

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