Reaktion #2486767

ord-93472d26c82947fca04307aa781dce04

Reaktionsgleichung

COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)NC(C)(C)C
N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide
[H][H]
hydrogen
→
COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C
N-tert-Butyl-5-amino-2-methoxycarbonylbenzenesulfonamide

Edukte

COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)NC(C)(C)C
N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide
[H][H]
hydrogen

Reagenzien

[Pd]
Pd-C

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe catalyst is separated off
  2. 2
    Sonstigethe solvent is removed by distillation
  3. 3
    Sonstigeto crystallize

Vorschrift

25.08 g (0.079 mol) of N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide are dissolved in 1000 ml of MeOH. 0.50 g of Pd-C (10%) is added and the mixture is shaken under a hydrogen atmosphere (1 atm) until the uptake of hydrogen has finished. The catalyst is separated off and the solvent is removed by distillation. The residue is induced to crystallize by stirring with a little ethyl acetate. The resulting N-tert-butyl-5-amino-2-methoxycarbonylbenzenesulfonamide (18.3 g; 80.9% of theory) melts at 193° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05449812uspto-grants-1995_09