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

HRID 1378835

Reaction equation

HRID 1378835 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 6483564{2-[2-(Hydroxyimino-phenyl-methyl)-phenyldisulfanyl]-phenyl}-phenyl-methanoneYield 35.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

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.;

Workup

  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

Sources & evidence

ORD record
ord-c3a96cf56fd54e0bbbaa3306347886dd
Source dataset
uspto-grants-1997_09
Patent number
US05668291

Linked notes

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