Ammonium Hydroxide → 3-Chloro-4-fluorobenzenesulfonamide

HRID 1597553Notes

Reaction equation

HRID 1597553 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[NH4+:14]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:14])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1452223-Chloro-4-fluorobenzenesulphonyl chloride

Product 1

HCID 75098833-Chloro-4-fluorobenzenesulfonamideYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-4-fluorobenzenesulfonyl chloride (2.29 g, 10 mmol) in methylene chloride (30 mL) was added 25% ammonium hydroxide (10 mL) at room temperature and the mixture was stirred for 1 hour. The solvent was removed in vacuo. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The resulting solid was recrystallized from ether-hexane to give the title compound (1.429 g, 68.2% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in ethyl acetate (50 mL)
  3. washthe whole washed with water and brine
  4. dry with materialAfter dried over MgSO4 and concentration in vacuo
  5. customThe resulting solid was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-f3e5329f00a440919170cbfd51a75303
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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