Hydroxylamine HCl → HCID 86759069, compound

HRID 1358156Notes

Reaction equation

HRID 1358156 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1.[Cl-].[OH:15][NH3+:16].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[N:16][OH:15])[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 18183644HCID 18183644, compound

Product 1

HCID 86759069HCID 86759069, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

9.72 g (50 mmol) of 1-(4-Methylsulfanyl-phenyl)-butane-1-one is dissolved in hot ethanol. Then a solution of hydroxylammonium chloride (3.58 g, 51.5 mmol) and sodium acetate (7.0 g, 85 mmol) in 20 ml of water is added, and the reaction solution is stirred at 100° C. for 4 hrs. After cooling and concentrating, water is added. The crude product is extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 0.98 (t, 3H), 1.54-1.64 (m, 2H), 2.50 (s, 3H), 2.76 (t, 2H), 7.24 (d, 2H), 7.54 (d, 2H), 7.98 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrating
  3. additionwater is added
  4. extractionThe crude product is extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as an eluent

Sources & evidence

ORD record
ord-9c3a7e05a2914a8592ad8ebf384207b8
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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