Hydrochloric Acid → {2-[2-(Hydroxyimino-phenyl-methyl)-phenyldisulfanyl]-phenyl}-phenyl-methanone

HRID 3747

Reaktionsgleichung

Reaktionsgleichung von HRID 3747
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:32][OH:33].Cl.C(OCC)(=O)C>C(O)C.N1C=CC=CC=1>[OH:33][N:32]=[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:24]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 18935315[2-(2-Benzoyl-phenyldisulfanyl)-phenyl]-phenylmethanone

Produkt 1

HCID 6483564{2-[2-(Hydroxyimino-phenyl-methyl)-phenyldisulfanyl]-phenyl}-phenyl-methanoneAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

The [2-(2-benzoyl-phenyldisulfanyl)-phenyl]phenyl-methanone (0.55 g, 1.2 mmol) was diluted with ethanol (5 mL) and anhydrous pyridine (5 mL). Hydroxylamine hydrochloride (1 g, 14 mmol) was added and the solution was refluxed for 90 minutes. The solution was cooled and poured into cold aqueous HCl (1N). Ethyl acetate was added, the layers were separated, and the organic portion was washed with brine, dried (MgSO4), and filtered. The filtrate was concentrated to dryness and the residue was triturated with 75% hexane/25% ethyl acetate to give the title compound (0.19 g, 32%) as a white solid, mp 191°-193° C.;

Aufarbeitung

  1. temperaturethe solution was refluxed for 90 minutes
  2. temperatureThe solution was cooled
  3. customthe layers were separated
  4. washthe organic portion was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness
  8. customthe residue was triturated with 75% hexane/25% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-169cfd162f7a4903b732bbd90fedb229
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05734081

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