N,N-diethyl-2-nitrobenzenesulfonamide → 2-Amino-N,N-diethylbenzenesulfonamide

HRID 1105748Notes

Reaction equation

HRID 1105748 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:12])=[O:11])([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 4229519N,N-diethyl-2-nitrobenzenesulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 128195982-Amino-N,N-diethylbenzenesulfonamideYield 104.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a pressure vessel a mixture of 133 g of o-nitro-N,N-diethylbenzenesulfonamide, 5 g of 10% palladium on carbon, and 500 ml of ethyl acetate was shaken at 130° under 500 psi hydrogen pressure until hydrogen was no longer absorbed. The reaction mixture was cooled and the catalyst filtered off. Evaporation of the solvent in-vacuo gave 123 g of o-amino-N,N-diethylbenzenesulfonamide as a viscous oil which slowly crystallized to a solid, m.p. 45°-51°.

Workup

  1. customwas no longer absorbed
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe catalyst filtered off
  4. customEvaporation of the solvent in-vacuo

Sources & evidence

ORD record
ord-26f3400be9384ad1bdc3a4d129cbc533
Source dataset
uspto-grants-1982_01
Patent number
US04310346

Reaction notes

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