Cesium carbonate → N-(4-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzamide

HRID 883944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883944
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.[SH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([S:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

Produkt 1

HCID 67040744N-(4-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the product of Example 49A (553 mg, 1.557 mmol) in anhydrous N,N-dimethylformamide (15 mL) was treated with 4-mercaptophenol (196 mg, 1.557 mmol) and cesium carbonate (1.015 g, 3.114 mmol) at room temperature, then heated at 100° under a nitrogen atmosphere for 3 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The residue was taken up in H2O (30 mL) and the pH adjusted to 3 with 1N aqueous HCl. The aqueous was extracted with ethyl acetate (2×50 mL), and the combined organic extracts washed with brine (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. The residue was purified by trituration with methylene chloride and silica gel flash chromatography with a gradient of 6% to 30% ethyl acetate/methylene chloride to give the product as a dark yellow solid (517 mg, 75%).

Aufarbeitung

  1. temperatureheated at 100° under a nitrogen atmosphere for 3 hours
  2. customthe solvent removed by rotary evaporation in vacuo
  3. extractionThe aqueous was extracted with ethyl acetate (2×50 mL)
  4. washthe combined organic extracts washed with brine (25 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by trituration with methylene chloride and silica gel flash chromatography with a gradient of 6% to 30% ethyl acetate/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-8913c85c530d40e696ce710b519ca54f
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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