Water → 5-Amino-n-tert.-butyl-2-dimethylaminocarbonylbenzenesulfonamide

HRID 2300973Notes

Reaction equation

HRID 2300973 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]([N:20]([CH3:22])[CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O>[Zn].CO>[NH2:15][C:13]1[CH:12]=[CH:11][C:10]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:7])=[O:8])[CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 15240543N-tert.-butyl-2-dimethylaminocarbonyl-5-nitro-benzenesulfonamide

Product 1

HCID 152405445-Amino-n-tert.-butyl-2-dimethylaminocarbonylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

23.6 g of zinc powder are added to a suspension of 22.0 g of N-tert.-butyl-2-dimethylaminocarbonyl-5-nitro-benzenesulfonamide (Example d), 18.2 g of ammonium chloride, 70 ml of water and 150 ml of methanol. The mixture is then stirred at 50° C. When the reaction has ended, the solid is filtered off. After the solid has been washed with ethyl acetate, the filtrate is concentrated, the residue is taken up in ethyl acetate and the mixture is washed with water. After drying over MgSO4, the organic phase is concentrated and the residue is washed with diisopropyl ether; yield: 17.5 g; m.p.: 205-208° C.

Workup

  1. filtrationthe solid is filtered off
  2. washAfter the solid has been washed with ethyl acetate
  3. concentrationthe filtrate is concentrated
  4. washthe mixture is washed with water
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe organic phase is concentrated
  7. washthe residue is washed with diisopropyl ether

Sources & evidence

ORD record
ord-28715f36ee6042f0a74ed3e6c7012e2f
Source dataset
uspto-grants-2002_12
Patent number
US06498253B1

Reaction notes

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