Octopamine → 4-(1-Hydroxy-2-(2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonate

HRID 253008

Reaktionsgleichung

Reaktionsgleichung von HRID 253008
[OH-:1].[Na+].[NH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[OH:6].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15]>O1CCOCC1>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH:5]([OH:6])[CH2:4][NH:3][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N+:14]([O-:16])=[O:15])(=[O:24])=[O:1])=[CH:8][CH:9]=1)(=[O:25])=[O:24])([O-:16])=[O:15]

Komponenten

5

Edukt 3

HCID 4581OctopamineHCID 14798Sodium HydroxideHCID 155402-Nitrobenzenesulfonyl chloride

Produkt 1

HCID 866312114-(1-Hydroxy-2-(2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A 1 N aqueous solution of sodium hydroxide (79.1 ml, 79.1 mmol) solution was added to a solution of 5 g (26.4 mmol) of 4-(2-amino-1-hydroxyethyl)phenol in dioxane (50 ml), and the mixture was stirred at room temperature for 5 min. 2-Nitrobenzenesulfonyl chloride (14.6 g, 65.9 mmol) was added to this solution, and the mixture was stirred at room temperature for 17 hr. Dioxane as the solvent was removed under the reduced pressure, and the residue was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 13.3 g (yield 97%) of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 17 hr
  2. customDioxane as the solvent was removed under the reduced pressure
  3. extractionthe residue was extracted with methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationwas then filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a17dec25ac14d9ba04d3633c5090ee7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07871982B2

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