Methyl 2-(2-nitrophenylthio)benzoate → Methyl 2-[(2-aminophenyl)sulfanyl]benzoate

HRID 746740

Reaktionsgleichung

Reaktionsgleichung von HRID 746740
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Komponenten

4

Edukt 1

HCID 57362693Methyl 2-(2-nitrophenylthio)benzoate

Produkt 1

HCID 614949Methyl 2-[(2-aminophenyl)sulfanyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 2-[(2-nitrophenyl)thio]benzoate (1.17 g, 4.04 mmol) in methanol (50 mL) was purged with nitrogen prior to the addition of 10% Pd/C catalyst (0.12 g). The mixture was again purged with nitrogen and then purged with hydrogen from a balloon. The mixture was stirred under hydrogen overnight. Additional amount of 10% Pd/C catalyst (0.24 g) was added, and the mixture was stirred under hydrogen overnight. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated. The residue was subjected to silica gel chromatography eluted with 100% DCM to provide methyl 2-[(2-aminophenyl)thio]benzoate as a yellow oil that crystallized over time. MS (ES, M+H+): 260.2

Aufarbeitung

  1. customThe mixture was again purged with nitrogen
  2. custompurged with hydrogen from a balloon
  3. additionAdditional amount of 10% Pd/C catalyst (0.24 g) was added
  4. stirringthe mixture was stirred under hydrogen overnight
  5. filtrationThe reaction mixture was filtered through a pad of celite
  6. concentrationthe filtrate was concentrated
  7. washeluted with 100% DCM

Quellen und Nachweise

ORD-Eintrag
ord-09f5e0874c464434b8a1ba85fc3edbbb
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393873B2

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