Réaction #1093

ord-5441fae977e64216866214e130a2476a

Équation de réaction

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

Réactifs

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

Réactifs

Aucun

Solvants

CO
MeOH

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe catalyst is separated off
  2. 2
    Autrethe solvent is removed by distillation
  3. 3
    Autreto crystallize

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723409uspto-grants-1998_03