Sodium Hydroxide → 4-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide

HRID 2209739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2209739
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[F:31])#[N:2].[OH-:32].[Na+].Cl.[NH2:35]O>C(O)C>[NH2:2][C:1](=[N:35][OH:32])[C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([N:20]([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:27][CH:28]=2)=[CH:5][C:4]=1[F:31]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 193814994-[5-(4-cyano-3-fluoro-phenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide

Produkt 1

HCID 543034514-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred solution of 4-[5-(4-cyano-3-fluoro-phenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide (360 mg, 0.84 mmol) in 1.7 mL of 1N sodium hydroxide (1.7 mmol) and 10 mL of ethanol is treated with hydroxylamine hydrochloride (120 mg, 1.7 mmol). After refluxing overnight, the reaction is concentrated in vacuo. The resulting material is purified by chromatography on silica gel (500 g) with 60-70% ethyl acetate/hexane as the eluent to afford 4-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide as a colorless foam;

Aufarbeitung

  1. temperatureAfter refluxing overnight
  2. concentrationthe reaction is concentrated in vacuo
  3. customThe resulting material is purified by chromatography on silica gel (500 g) with 60-70% ethyl acetate/hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-3ed75856c8124fa28a37bbcbaf7465c7
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455274

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