Sodium 2-propanethiolate → 1-[1-(Isopropylthio)ethyl]-2-nitrobenzene

HRID 1176015Notizen

Reaktionsgleichung

Cl[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])[CH3:3].[CH3:13][CH:14]([S-:16])[CH3:15].[Na+]>C(#N)C>[CH:14]([S:16][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])[CH3:3])([CH3:15])[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

In a 1 liter three-necked flask equipped with a stirrer, dropping funnel and thermometer, 63 g 1-(1-chlorethyl)-2-nitrobenzene (VIII-1) (purity 99.4%, 0.337 mols) in 20 ml acetonitrile are added dropwise at 30-40° C. to 34.8 g (0.354 mol) sodium 2-propanethiolate in 450 ml acetonitrile. The suspension is stirred at 40° C. for another 16 hours, then cooled, and the solvent is removed under vacuum. The residue remaining is dissolved in dichloromethane, washed, dried over sodium sulfate, and the solvent is removed under vacuum. The crude product is purified by column chromatography (silica gel, 29:1 hexane/acetone). 48 g (98.8% purity by HPLC, 62.4% theoretical yield) of 1-[1-(isopropylthio)ethyl]-2-nitrobenzene are obtained as a yellow oil [logP (pH 2.3)=3.89].

Aufarbeitung

customIn a 1 liter three-necked flask equipped with a stirrer
temperaturecooled
customthe solvent is removed under vacuum
dissolutionThe residue remaining is dissolved in dichloromethane
washwashed
dry with materialdried over sodium sulfate
customthe solvent is removed under vacuum
customThe crude product is purified by column chromatography (silica gel, 29:1 hexane/acetone)

Quellen und Nachweise

ORD-Eintrag: ord-dfa85f38418743b5898c9a7f6702a799
Quelldatensatz: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07842710B2

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