Ethanol → HCID 66935159, compound

HRID 554770Notes

Reaction equation

HRID 554770 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11](=O)[CH2:12][CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C(O)C.C([O-])(=O)C.[Na+].[ClH:23].[NH2:24]O>O.C(OCC)(=O)C>[ClH:23].[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]([NH2:24])[CH2:12][CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 59496931HCID 59496931, compound

Product 1

HCID 66935159HCID 66935159, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To 1-(3-methane sulfonylphenyl)propan-1-one (188 g), ethanol (4.7 ml), sodium acetate (1.09 g), and hydroxylamine hydrochloride (0.68 g) were added and the mixture was stirred at 90° C. for 3 hours. Ethyl acetate and water were added to the reaction solution, the mixture was separated, then the organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained 1-(3-methane sulfonylphenyl)propan-1-one oxime was used instead of the starting material compound 1-(4-aminophenyl)propan-1-on oxime of Reference Example 109 for the similar procedure as with Reference Example 109 to obtain the title compound.

Workup

  1. customthe mixture was separated
  2. washthe organic layer was successively washed with saturated saline
  3. dry with materialdried over with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c3fa3760d11e40b496d0bddbdb2cea2b
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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