Nitric Acid → 2,6-Dichloro-3-nitrobenzene-1-sulfonamide

HRID 2301490Notes

Reaction equation

HRID 2301490 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[N+:13]([O-])([OH:15])=[O:14].O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([NH2:12])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 27580592,6-Dichlorobenzenesulfonamide

Product 1

HCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamideYield 76.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Into a solution of 2,6-dichlorobenzenesulfonamide (7.8 g, 34.5 mmol) in 30 mL of concentrated sulfuric acid at 0°, nitric acid (1.74 mL, 41.4 mmol) was added dropwise. The mixture was stirred at 02 C., for 2 hours, then 200 mL of water was added to produce a precipitate. The resulting mixture was filtered. The white solid was collected, washed with water and dried in vacuo to give the desired product (7.17 g, 76%). 1H NMR (DMSO-d6): δ 8.25 (s, 2H), 8.20 (d, 1H), 7.92 (d, 1H).

Workup

  1. customto produce a precipitate
  2. filtrationThe resulting mixture was filtered
  3. customThe white solid was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bdaeec21f1054abe851072b7b0ae9764
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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