2-Chloro-N-(2-hydroxy-ethyl)-5-(2-oxo-propyl)-benzenesulfonamide → N-(2-Hydroxy-ethyl)-3-(2-oxo-propyl)-benzenesulfonamide

HRID 908180Notes

Reaction equation

HRID 908180 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12]([NH:15][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13]>CO.[Pd]>[OH:18][CH2:17][CH2:16][NH:15][S:12]([C:3]1[CH:2]=[CH:7][CH:6]=[C:5]([CH2:8][C:9](=[O:11])[CH3:10])[CH:4]=1)(=[O:14])=[O:13]

Participants

4

Reactant 1

HCID 673909962-Chloro-N-(2-hydroxy-ethyl)-5-(2-oxo-propyl)-benzenesulfonamide

Product 1

HCID 67391502N-(2-Hydroxy-ethyl)-3-(2-oxo-propyl)-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Chloro-N-(2-hydroxy-ethyl)-5-(2-oxo-propyl)-benzenesulfonamide (43b) (1.22 g, 4.18 mmol) in methanol (150 ml) is stirred under an atmosphere of hydrogen in the presence of 10% Palladium on carbon (1 g) for 5 hours at room temperature. Filtration through celite and removal of the solvent affords the titled compound which is purified by chromatography on silica eluting with ethyl acetate-hexane (2:1).

Workup

  1. filtrationFiltration
  2. customthrough celite and removal of the solvent

Sources & evidence

ORD record
ord-086a9253e7754bf3b7581ef51d640f51
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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