Chlorosuccinimide → Ethyl 2-chloro-2-[2-(4-methoxyphenyl)hydrazono]acetate

HRID 896803

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:2].[Cl:17]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[C:5]([Cl:17])=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 2.5 °C

Versuchsvorschrift

Method A. A solution of [(4-methoxyphenyl)hydrazono]acetic acid ethyl ester (33, 4.0 g, 18.0 mmol) in anhydrous THF (40 mL) was treated with N-chlorosuccinimide (NCS, 2.52 g, 18.9 mmol, 1.05 equiv) at 0-5° C. under N2, and the resulting reaction mixture was stirred at 0-5° C. for an additional 30 min before being gradually warmed to 25° C. for 12 h. When HPLC and TLC showed the reaction was deemed complete, the solvent was removed in vacuo. The residue was directly purified by column chromatography (SiO2, 0-25% EtOAc/hexane gradient elution) to afford the desired chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester (34, 3.51 g, 4.62 g theoretical, 76%) as pale-yellow solids, which was found to be essentially pure to do the following reaction without further purification. For 34, CIMS m/z 255/257 (M+−H, C11H13ClN2O3).

Aufarbeitung

customthe resulting reaction mixture
temperaturebefore being gradually warmed to 25° C. for 12 h
customthe solvent was removed in vacuo
customThe residue was directly purified by column chromatography (SiO2, 0-25% EtOAc/hexane gradient elution)

Quellen und Nachweise

ORD-Eintrag: ord-faaa910d7ff54efdb3b96a45e6efe9a5
Quelldatensatz: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06919451B2

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