Water → Methyl 4-(4-aminophenylthio)-3-nitrobenzoate
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.O(C(C)C)C(C)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:22][C:19]2[CH:20]=[CH:21][C:16]([NH2:15])=[CH:17][CH:18]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
A mixture of 4-chloro-3-nitrobenzoic acid methyl ester (15.0 g, 68 mmol), 4-aminothiophenol (8.8 g, 68 mmol) and K2CO3 (11.8 g, 85 mmol) in DMF (150 mL) was heated at 90° C. for 1.5 hours, cooled to room temperature, and then poured into H2O (450 mL) under stirring. The aqueous mixture was extracted with ethyl acetate (400 mL). The extract was washed with H2O (3 times) and brine, dried over MgSO4, and evaporated to give the crude produce as orange crystal. The crude product was suspended in 150 mL of i-Pr2O and stirred at room temperature for 1 hour. The crystal was collected by filtration, washed with i-Pr2O and dried at 60° C. for 3 days under reduced pressure gave purified title compound as orange crystal (18.6 g, 90% yield).
Aufarbeitung
- temperaturecooled to room temperature
- extractionThe aqueous mixture was extracted with ethyl acetate (400 mL)
- washThe extract was washed with H2O (3 times) and brine
- dry with materialdried over MgSO4
- customevaporated
- customto give the crude
- customproduce as orange crystal
- stirringstirred at room temperature for 1 hour
- filtrationThe crystal was collected by filtration
- washwashed with i-Pr2O
- customdried at 60° C. for 3 days under reduced pressure
- customgave
Quellen und Nachweise
- ORD-Eintrag
- ord-0d736717c6b949b4abecc32bd1afd42c
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09249138B2
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