Reaction #3843

Reaction equation

Ethyl acetate

[2-(2-benzoyl-phenyldisulfanyl)-phenyl]phenyl-methanone

Hydroxylamine hydrochloride

HCl

→

title compound

Yield 35.9%

{2-[2-(hydroxyimino-phenyl-methyl)-phenyldisulfanyl]phenyl}-phenyl-methanon

Yield 35.9%

Solvents

ethanol

pyridine

Conditions

Workup

1. 1
   Temperaturethe solution was refluxed for 90 minutes
2. 2
   TemperatureThe solution was cooled
3. 3
   Otherthe layers were separated
4. 4
   Washthe organic portion was washed with brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated to dryness
8. 8
   Otherthe residue was triturated with 75% hexane/25% ethyl acetate

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.;

Source