Ammonia → Benzenesulfonamide, 3-nitro-

HRID 1890991Notes

Reaction equation

HRID 1890991 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH3:14].C(=O)([O-])[O-].[NH4+].[NH4+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH2:14])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 84763-Nitrobenzenesulfonyl chlorideHCID 517111Ammonium Carbonate

Product 1

HCID 67138Benzenesulfonamide, 3-nitro-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Nitro-benzenesulfonyl chloride (2.0 g, 9.0 mmol) was dissolved in acetonitrile (20 mL). To this solution was added concentrated aqueous ammonia (20 mL) saturated with ammonium carbonate and the reaction mixture was vigorously stirred for 1 h at room temperature. Then acetonitrile was removed under reduced pressure and the residue diluted with cold water (30 mL) leading to a precipitate formation. The precipitate was filtered out and washed with water (2×15 mL), ether and dried. Yield of 3-nitro-benzenesulfonamide 1.46 g (80%). Beige powder.

Workup

  1. customThen acetonitrile was removed under reduced pressure
  2. additionthe residue diluted with cold water (30 mL)
  3. filtrationThe precipitate was filtered out
  4. washwashed with water (2×15 mL), ether
  5. customdried

Sources & evidence

ORD record
ord-d36b25d89cde4ed0bfdb78b0895f610f
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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