2-Chloro-5-nitrobenzenesulfonamide → 2-Amino-5-nitrobenzenesulfonamide

HRID 2374411Notes

Reaction equation

HRID 2374411 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].C(=O)([O-])[O-].[NH4+:19].[NH4+]>[OH-].[NH4+].S([O-])([O-])(=O)=O.[Cu+2]>[NH2:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 667842-Chloro-5-nitrobenzenesulfonamideHCID 517111Ammonium Carbonate

Product 1

HCID 153583862-Amino-5-nitrobenzenesulfonamideYield 36.6%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-5-nitrobenzenesulfonamide (Example 17a, 0.88 g, 3.72 mmol), ammonium carbonate (0.88 g, 9.16 mmol), and copper (II) sulfate (0.175 g, 1.10 mmol) in concentrated aqueous ammonium hydroxide solution (4.4 mL) was heated for 4 h at 120° C. in a pressure reaction vessel. The mixture was allowed to cool to 25° C. and the resulting solid was collected by vacuum filtration, washed with water and dried to afford the desired product, 2-amino-5-nitrobenzenesulfonamide (0.295 g, 1.36 mmol, 36.5% yield) as a tan solid.

Workup

  1. temperatureto cool to 25° C.
  2. filtrationthe resulting solid was collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6a69e6950d97497c9e13ca51d1302be6
Source dataset
uspto-grants-2008_12
Patent number
US07462611B2

Reaction notes

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