Cesium carbonate → N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide

HRID 605289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605289
Cl[C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:18])=[C:6]([NH:8][C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1.[SH:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:29][C:26]1[CH:27]=[CH:28][C:23]([S:22][C:2]2[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:18])=[C:6]([NH:8][C:9](=[O:17])[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:7]=2)=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 2907847N-(5-chloro-2-methyl-4-nitrophenyl)-2-phenylacetamide

Produkt 1

HCID 67041085N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product from Example 265A (0.305 g, 1.0 mmol), 4-mercaptophenol (0.151 g, 1.2 mmol, 1.2 eq) and cesium carbonate (0.782 g, 2.4 mmol, 2.4 eq) in dimethyl formamide (10 mL) was heated at 110° C. for 2 h, cooled to room temperature, and poured over ice water (100 mL). This mixture was extracted with ethyl acetate (3×150 mL) and the combined organic phases were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by chromatography on silica gel eluting with 1:1 hexane/ethyl acetate to provide the title compound as a yellow solid (0.282 g, 72%).

Aufarbeitung

  1. extractionThis mixture was extracted with ethyl acetate (3×150 mL)
  2. washthe combined organic phases were washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with 1:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bd57b1622be445fcb574be2ec28d0f8d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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