3,5-Dinitrobenzenesulfonamide → 3-Amino-5-nitrobenzenesulfonamide

HRID 1957958Notes

Reaction equation

HRID 1957958 reaction equation
O.S.[Na].[N+:4]([C:7]1[CH:8]=[C:9]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)([O-])=O>CO>[NH2:4][C:7]1[CH:8]=[C:9]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1

Participants

4

Reactant 2

HCID 35884373,5-DinitrobenzenesulfonamideHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 592861913-Amino-5-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of sodium hydrogensulfide hydrate (3.88 g; 49 mmol) in Methanol (200 ml) was added to a solution of 3,5-dinitro-benzenesulfonamide (6 g; 24.27 mmol) in Methanol (500 ml). The reaction mixture was refluxed for 3 h then cooled to room temperature, filtered and concentrated in vacuo. The crude was washed with water, filtered and dried in vacuo. 3.2 g (15 mmol; 61% yield) of orange powder were obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. washThe crude was washed with water
  5. filtrationfiltered
  6. customdried in vacuo
  7. custom3.2 g (15 mmol; 61% yield) of orange powder were obtained

Sources & evidence

ORD record
ord-4a66b42d129c4cb7b46ba86a80fda940
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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