Diethyl dithiophosphate, potassium salt → 2'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester

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Reaktionsgleichung

P(OCC)(OCC)([S-])=[S:2].[CH3:10][O:11][C:12]([C:14]1[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[CH:16][CH:17]=[C:18]([C:20]#[N:21])[CH:19]=1)=[O:13]>C1COCC1.O>[CH3:10][O:11][C:12]([C:14]1[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[CH:16][CH:17]=[C:18]([C:20](=[S:2])[NH2:21])[CH:19]=1)=[O:13]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

O,O′-Diethyl dithiophosphate (available from Aldrich Chemical Company, Inc.; 6.85 g, 36.8 mmol) was added to a solution of compound 4-cyano-2′-nitro-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 3; 8.62 g, 30.5 mmol) in a mixture of THF (96 mL) and water (24 mL). The resulting mixture was stirred at 80° C. for 45 h and then evaporated to a small volume. Ethyl acetate (500 mL) was added and the mixture was washed with water (250 mL) and sat. NaHCO3 (250 mL), dried over anhydrous sodium sulfate, filtered, evaporated, and purified by silica gel chromatography, using 17-50% ethyl acetate/petroleum ether as eluent, to give 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (5.0 g, 52%). 1H NMR (300 MHz, CDCl3) δ 8.50 (d, J=2.1 Hz, 1H), 8.18-8.15 (m, 2H), 7.70-7.54 (m, 3H), 7.32 (s, 1H), 7.30 (s, 1H), 7.24 (d, J=1.2 Hz, 1H), 3.69 (s, 3H).

Aufarbeitung

customevaporated to a small volume
additionEthyl acetate (500 mL) was added
washthe mixture was washed with water (250 mL) and sat. NaHCO3 (250 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-f807f09ddd5143e3810c0ecbe0c00424
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09073881B2

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