N,N-Diethyl-4-nitrobenzenesulfonamide → 4-amino-N,N-diethylbenzene-1-sulfonamide

HRID 2186767Notes

Reaction equation

HRID 2186767 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 745341N,N-Diethyl-4-nitrobenzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 950674-amino-N,N-diethylbenzene-1-sulfonamideYield 106.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 250 mL Parr shaker bottle was charged with 4-nitro-N,N-diethyl-benzenesulfonamide (617 mg, 2.39 mmol), ethyl acetate (50 mL), and 10% palladium on activated carbon (100 mg). The bottle was place on a Parr shaker apparatus and charged with hydrogen to a pressure of 52 psi. The reaction mixure was shaken for two hours, filtered through celite, and concentrated to provide 4-Amino-N,N-diethyl-benzenesulfonamide as a green solid (581 mg).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d151dc3d525f494c996884bab6568409
Source dataset
uspto-grants-2002_06
Patent number
US06407120B1

Reaction notes

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