Sodium hydride → O-2-carbomethoxy-4-fluorophenyl dimethylthiocarbamate

HRID 974197

Reaktionsgleichung

[F:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[S:20]>CN(C)C=O.O>[CH3:17][N:18]([CH3:22])[C:19](=[S:20])[O:12][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of methyl 5-fluorosalicylate (3.93 g, 23.1 mmol) in dry N,N-dimethylformamide (30 ml) was added sodium hydride (1.1 g, 50% oil dispersion). After hydrogen gas evolution had ceased, the mixture was cooled in an ice-bath, and dimethylthiocarbamoyl chloride (3.71 g, 30.0 mmol) was added. The mixture was stirred at 80° C. for one hour, cooled, and poured into water (100 ml). The product was extracted with diethyl ether (2×), and the combined organic extracts were washed with water, 5% aqueous potassium hydroxide, water, dried (sodium sulfate), and evaporated. The solid obtained was recrystallized from diethyl ether-hexane to afford 3.16 g (53%) of O-2-carbomethoxy-4-fluorophenyl dimethylthiocarbamate. The 90 MHz NMR spectrum in chloroform-d was in accord with the desired structure.

Aufarbeitung

temperaturethe mixture was cooled in an ice-bath
temperaturecooled
extractionThe product was extracted with diethyl ether (2×)
washthe combined organic extracts were washed with water, 5% aqueous potassium hydroxide, water
dry with materialdried (sodium sulfate)
customevaporated
customThe solid obtained
customwas recrystallized from diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag: ord-27f5574cb8c34a04a0a1bc573578e5a4
Quelldatensatz: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05068248

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