Hydrochloric Acid → 4-Fluoro-3-nitrobenzenesulfonamide

HRID 405670Notes

Reaction equation

HRID 405670 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].Cl[S:12]([OH:15])(=O)=[O:13].[NH4+:16].[OH-].Cl>CC(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:12]([NH2:16])(=[O:15])=[O:13])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24638Chlorosulfonic acidHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

Following the procedure of J. Med. Chem. 2006, 49, 1173, a solution of commercially available 2-fluoronitrobenzene (10.00 g, 70.87 mmol) and chlorosulfonic acid (21 mL) were heated to reflux for 18 hours at 95° C. and then cooled to room temperature. The solution was then added dropwise over a 1 hour period to a solution of iPrOH (225 mL) and concentrated aqueous NH4OH (54 mL) at −35° C. and stirred for 0.5 hours. The solution was maintained at −35° C. while concentrated aqueous HCl was added until the pH was acidic. The solution was then evaporated to remove some iPrOH, water was added and the solution was evaporated again to remove most of the iPrOH. More water was added, the solution was filtered and the solid was washed with 1 N aqueous HCl and water to give the title compound.

Workup

  1. temperaturecooled to room temperature
  2. additionwas added until the pH
  3. customThe solution was then evaporated
  4. customto remove some iPrOH, water
  5. additionwas added
  6. customthe solution was evaporated again
  7. customto remove most of the iPrOH
  8. additionMore water was added
  9. filtrationthe solution was filtered
  10. washthe solid was washed with 1 N aqueous HCl and water

Sources & evidence

ORD record
ord-4aacd1ef64ca43638829d479acdec000
Source dataset
uspto-grants-2014_06
Patent number
US08753857B2

Reaction notes

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