4-Methoxybenzylamine → 5-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid methyl ester

HRID 1366215

Reaktionsgleichung

Reaktionsgleichung von HRID 1366215
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:10])[O:7][C:6]=1[CH2:11]Br)=[O:4].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1>CO>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:10])[O:7][C:6]=1[CH2:11][NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 754524-MethoxybenzylamineHCID 15534191Methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate

Produkt 1

HCID 590231235-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-2-bromomethyl-furan-3-carboxylic acid methyl ester (1.74, 5.88 mmol) and p-methoxy benzylamine (0.76 mL, 5.88 mmol) in MeOH (30 mL) is stirred at 85° C. for 1.5 hours. The reaction mixture is concentrated in vacuo and the residue purified by silica gel column chromatography eluting with 4:1 petroleum ether:ethyl acetate followed by 1:1 petroleum ether:ethylacetate. The title compound is isolated (643.8 mg).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue purified by silica gel column chromatography
  3. washeluting with 4:1 petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-e930bd0f854a463d8e3859144d92c6cc
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893058B2

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