methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate → methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

HRID 997

Reaction equation

HRID 997 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 15240542methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 10946074methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customThe catalyst is separated off
  2. customthe solvent is removed by distillation
  3. customto crystallize

Sources & evidence

ORD record
ord-5441fae977e64216866214e130a2476a
Source dataset
uspto-grants-1998_03
Patent number
US05723409

Linked notes

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