Benzyl Bromide → HCID 101859068, Verbindung

HRID 58859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58859
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=O>C(#N)C.CCOC(C)=O>[CH2:7]([N:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:15]=[CH:27][S:24]1(=[O:26])=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 115793042-(Methylsulfonamido)benzaldehyde

Produkt 1

HCID 101859068HCID 101859068, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Cesium carbonate (18.0 g, 55 mmol) and benzyl bromide (6.6 mL, 55 mmol) were added to a solution of N-(2-formylphenyl)methanesulfonamide (5.50 g, 27.6 mmol) in acetonitrile (120 mL). The reaction mixture was heated at 60° C. for 16 h and then cooled to ambient temperature. The mixture was diluted with EtOAc (200 mL) and filtered. The filtration cake was washed with EtOAc (200 mL) and the combined organics were concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:5) to afford 1-benzyl-1H-benzo[c][1,2]thiazine 2,2-dioxide (6.5 g, 87% yield) as a colorless oil.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered
  3. washThe filtration cake was washed with EtOAc (200 mL)
  4. concentrationthe combined organics were concentrated
  5. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-e6c18c22b4ee4b0492e7c9404d37af24
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434761B2

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