Reacción #1093

ord-5441fae977e64216866214e130a2476a

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CO
MeOH

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe catalyst is separated off
  2. 2
    Otrothe solvent is removed by distillation
  3. 3
    Otroto crystallize

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723409uspto-grants-1998_03