N-[3-(4-Nitro-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide → N-[3-(4-Amino-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide

HRID 2088795Notes

Reaction equation

HRID 2088795 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)=[CH:6][C:5]=1[CH2:27][NH:28][CH2:29][CH2:30][CH3:31])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)=[CH:6][C:5]=1[CH2:27][NH:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 1

HCID 58625103N-[3-(4-Nitro-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide

Product 1

HCID 58625143N-[3-(4-Amino-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[3-(4-nitro-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide (0.0016 mol) in methanol (50 mL) was hydrogenated with 10% Pd/C (0.1 g) as a catalyst. After uptake of H2 gas (3 equiv.), the catalyst was filtered off and the filtrate was evaporated to yield the title compound as a residue. (The product was used in subsequent steps without further purification.)

Workup

  1. filtrationAfter uptake of H2 gas (3 equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-24cc7da9bffb47848c5849f820282aa4
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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