Ethanol → (S)-N-(4-(Oxiran-2-ylmethoxy)phenyl)methanesulfonamide

HRID 1281478Notes

Reaction equation

HRID 1281478 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1C=CC=C[CH:3]=1.[H][H].C([OH:24])C>[Pd]>[O:24]1[CH2:3][C@H:2]1[CH2:1][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 669037N-(4-phenylmethoxyphenyl)methanesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 11322479(S)-N-(4-(Oxiran-2-ylmethoxy)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N-[4-(Benzyloxy)phenyl]methanesulfonamide (3.0 g, 10.8 mmol) was dissolved in ethanol (150 mL). 10% Palladium on carbon (0.3 g) was added and the mixture shaken overnight under 50 psi hydrogen on a Parr apparatus. The solution was filtered through a Celite pad and the solvent removed to yield the title compound (1.32 g, 7.4 mmol).

Workup

  1. filtrationThe solution was filtered through a Celite pad
  2. customthe solvent removed

Sources & evidence

ORD record
ord-eabd99f35814487eaeb1cd226ed336db
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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