Benzamide → N-(4-bromobenzenesulfonyl)benzamide

HRID 1823109

Reaktionsgleichung

Reaktionsgleichung von HRID 1823109
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>O1CCCC1.C(OCC)(=O)C.O>[C:1]([NH:9][S:19]([C:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][CH:15]=1)(=[O:21])=[O:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 2331BenzamideHCID 7396p-Bromobenzenesulfonyl chlorideHCID 24758Sodium hydride

Produkt 1

HCID 766162N-(4-bromobenzenesulfonyl)benzamideAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of benzamide (1.42 g) in tetrahydrofuran (50 ml) were added sodium hydride (611 mg) and 4-bromobenzenesulfonyl chloride (3.0 g), and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give N-benzoyl-4-bromobenzenesulfonamide (2.1 g) as a colorless powder.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-85d33e726aff4a14a934199ed9221887
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037938B2

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