4-Aminothiophenol → Methyl 4-(4-aminophenylthio)-3-nitrobenzoate

HRID 884006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884006
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+]>C(O)C.C(OCC)(=O)C>[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 145104-AminothiophenolHCID 517045Sodium AcetateHCID 735797Methyl 4-chloro-3-nitrobenzoate

Produkt 1

HCID 59376804Methyl 4-(4-aminophenylthio)-3-nitrobenzoateAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 4-chloro-3-nitrobenzoate (1.00 g, 4.638 mmol) in anhydrous ethanol (40 mL) was treated with 4-aminothiophenol (0.813 g, 6.494 mmol) and anhydrous sodium acetate (1.90 g, 23.19 mmol) at room temperature under a nitrogen atmosphere, at reflux for 2 hours. The reaction was cooled, diluted with ethyl acetate (100 mL), and washed with water (3×50 mL) and brine (50 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. The resulting orange solid was triturated with ethyl ether/hexanes (1:1 v/v, 3×30 mL), and dried in vacuo to afford the title compound (1.36 g, 4.469 mmol, 96%). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.87 (s, 3 H) 5.80 (s, 2 H) 6.70 (d, J=8.46 Hz, 2 H) 7.00 (d, J=8.46 Hz, 1 H) 7.23 (d, J=8.46 Hz, 2 H) 8.05 (dd, J=8.46, 1.84 Hz, 1 H) 8.64 (d, J=1.84 Hz, 1 H). MS (ESI+) m/z 305 (M+H)+.

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. temperatureThe reaction was cooled
  3. washwashed with water (3×50 mL) and brine (50 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe resulting orange solid was triturated with ethyl ether/hexanes (1:1 v/v, 3×30 mL)
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36ababdbfc184bf5b4da00007770c0f5
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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