Silica → N-[3-(4-Amino-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide

HRID 1968857Notes

Reaction equation

HRID 1968857 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:12]2[CH:13]=[C:14]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:6][C:5]=1[CH2:28][NH:29][CH2:30][CH2:31][CH3:32])([O-])=O.O=[Si]=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:12]2[CH:13]=[C:14]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:6][C:5]=1[CH2:28][NH:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 2

HCID 24261SilicaHCID 58625145N-[3-(4-Nitro-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide

Product 1

HCID 58625094N-[3-(4-Amino-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[3-(4-nitro-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide (0.0019 mol) in methanol (100 mL) was hydrogenated with 10% Pd/C (0.5 g) as a catalyst. After uptake of H2 (3 equiv.), the reaction mixture was filtered over Dicalite, and the filtrate was evaporated. The residue was filtered over silica gel (eluent: 95:5 CH2Cl2:CH3OH),and then the purest product fractions were collected, and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. customthe filtrate was evaporated
  2. filtrationThe residue was filtered over silica gel (eluent: 95:5 CH2Cl2:CH3OH)
  3. customthe purest product fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ab3c42828fb64841bb5038d9cb656898
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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