Water → N-benzhydryl-4-(bromomethyl)benzenesulfonamide

HRID 40790

Reaktionsgleichung

Reaktionsgleichung von HRID 40790
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.O>ClCCl>[CH:1]([NH:14][S:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][Br:22])=[CH:29][CH:28]=1)(=[O:31])=[O:32])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Produkt 1

HCID 67021864N-benzhydryl-4-(bromomethyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzhydrylamine (640 μL) was dissolved in dichloromethane (5.0 mL). To the solution, triethylamine (645 μl) and 4-(bromomethyl)benzenesulfonyl chloride (1.0 g) were added at 0° C., and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, water (10 mL) was added, and the resultant mixture was then extracted with chloroform (30 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40% ethyl acetate/hexane) to obtain the title compound (753 mg).

Aufarbeitung

  1. extractionthe resultant mixture was then extracted with chloroform (30 mL)
  2. washThe organic layer was washed with brine (15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-39757e3b8a604a86b768458e01915af5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530490B2

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