Oxygen → N-(3-Oxo-1-phenylpropyl)benzenesulfonamide

HRID 860169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860169
O=[O+][O-].[C:4]1([CH:10]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH:12]=C)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:24]=O.S(C)C>C(Cl)Cl>[O:24]=[CH:12][CH2:11][CH:10]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 10946112N-(1-phenylbut-3-enyl)benzenesulfonamide

Produkt 1

HCID 86590616N-(3-Oxo-1-phenylpropyl)benzenesulfonamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stream of ozone was passed through a solution of the product of Step 3 (1.9 g, 6.6 mmol) in CH2Cl2 (90 mL) at −78° C. for 1 h. The solution was then purged with oxygen, Me2S (1.1 mL, 15 mmol) was added, the cooling bath removed and the mixture allowed to warm to RT. The reaction was complete after 3 days and the solvent removed under reduced pressure and the mixture purified by column chromatography on silica eluting 5–10% MeOH/CH2Cl2 to give the benzenesulfonamide as a colourless oil (1.6 g, 84%). 1H NMR (360 MHz, CDCl3) δ 2.90–3.10 (2H, m), 4.79–4.86 (1H, m), 5.45 (1H, d, J=7.4 Hz), 7.03–7.09 (2H, m), 7.13–7.18 (3H, m), 7.35–7.39 (2H, m), 7.46–7.51 (1H, m), 7.69–7.71 (2H, m), 9.64 (1H, s).

Aufarbeitung

  1. additionwas added
  2. customthe cooling bath removed
  3. customthe solvent removed under reduced pressure
  4. customthe mixture purified by column chromatography on silica eluting 5–10% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e1ae9faa7a1b4059b646ffda8ca2f00c
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153868B2

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