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

HRID 1177045Notes

Reaction equation

HRID 1177045 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-c14c3ffcb5dd4d12a3ad9baddb602dca
Source dataset
uspto-grants-2010_11
Patent number
US07842838B2

Reaction notes

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