Dimethyl Sulfoxide → N-(3-formylphenyl)-2-methoxyacetamide

HRID 639713

Reaktionsgleichung

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][CH2:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][OH:21])=[O:15].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][CH2:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

To a mixture of 11.40 g of oxalyl chloride and 200 ml of dichloromethane was added dropwise a solution of 14 ml of dimethyl sulfoxide in 30 ml of dichloromethane at −60° C. for 15 minutes. After stirred at −60° C. for 10 minutes, a solution of 15.88 g of 3-(methoxyacetylamino)benzyl alcohol in 70 ml of dichloromethane was added dropwise at −60° C. for 20 minutes. After stirred at −60° C. for 10 minutes, 24.82 g of triethylamine was added dropwise at −60° C. for 20 minutes. After stirred at room temperature for 45 minutes, 500 ml of water was added to the reaction solution, followed by extraction with 300 ml of ethyl acetate. The organic layer washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated to obtain 14.93 g of 3-(methoxyacetylamino)benzaldehyde [Compound No. (a)] as a white crystal.

Aufarbeitung

stirringAfter stirred at −60° C. for 10 minutes
stirringAfter stirred at room temperature for 45 minutes
extractionfollowed by extraction with 300 ml of ethyl acetate
washThe organic layer washed with an aqueous saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-7cbf437d179841f690e3d686017de98a
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07691883B2

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