Imidazole → 2-Amino-5-[(tert-butyldimethylsilyl)oxy]benzoic acid

HRID 324519

Reaktionsgleichung

Reaktionsgleichung von HRID 324519
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][C:15]1[CH:23]=[C:19]([C:20]([OH:22])=[O:21])[C:18]([NH2:24])=[CH:17][CH:16]=1>CN(C)C=O>[NH2:24][C:18]1[CH:17]=[CH:16][C:15]([O:14][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])=[CH:23][C:19]=1[C:20]([OH:22])=[O:21]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1645925-Hydroxyanthranilic acid

Produkt 1

HCID 220044712-Amino-5-[(tert-butyldimethylsilyl)oxy]benzoic acidAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (1.8 g, 26.1 mmol) and tert-butyldimethylsilyl chloride (3.95 g, 26.1 mmol) were added to a solution of the commercially available 5-hydroxyanthranilic acid (1.0 g, 6.54 mmol) in dimethylformamide (40 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 18 hours. Aqueous work-up afforded an impure sample of 2-amino-5-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1.74 g) that was used in Step (ii) without further purification.

Aufarbeitung

  1. temperaturewhile cooling in an ice/water bath

Quellen und Nachweise

ORD-Eintrag
ord-4551e05f3b724432ba1591d5a84c18aa
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218393B1

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