Reaction #1093

ord-5441fae977e64216866214e130a2476a

Reaction equation

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

Reactants

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

Reagents

None

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe catalyst is separated off
  2. 2
    Otherthe solvent is removed by distillation
  3. 3
    Otherto crystallize

Procedure

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.v1Patent: US05723409uspto-grants-1998_03