Chlorosulfonic acid → 4-Amino-3-bromo-5-nitrobenzenesulfonyl chloride

HRID 2216220Notes

Reaction equation

HRID 2216220 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11](N)(=[O:13])=[O:12])=[CH:4][C:3]=1[Br:15].[Cl:16]S(O)(=O)=O>>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([Cl:16])(=[O:13])=[O:12])=[CH:4][C:3]=1[Br:15]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 218864374-Amino-3-bromo-5-nitrobenzenesulfonamide

Product 1

HCID 218861144-Amino-3-bromo-5-nitrobenzenesulfonyl chloride

Procedure

4-Amino-3-bromo-5-nitrobenzenesulfonamide ((U.S. Pat. No. 3,987,199) 1 g, 3.17 mmol) was heated at 95° C. for 3 h in chlorosulfonic acid (10 mL). The solution was cooled then poured onto ice and then filtered. The solid was redissolved in DCM and dried over sodium sulfate. Removal of the solvent yielded the product (960 mg) which was used without further purification.

Workup

  1. temperatureThe solution was cooled
  2. additionthen poured onto ice
  3. filtrationfiltered
  4. dissolutionThe solid was redissolved in DCM
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-607bd1a3adcc4d15a92f53dc37e6714b
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

Loading…