Ammonium Hydroxide → 3,5-Difluorobenzenesulfonamide

HRID 83899

Reaction equation

HRID 83899 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH4+:13].[OH-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:13])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27740583,5-Difluorobenzenesulfonyl chloride

Product 1

HCID 4462753,5-DifluorobenzenesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-difluorobenzenesulfonyl chloride (25 g, 0.117 mol) in THF (150 mL) was added 35% aq. NH4OH (120 mL) over 1 h in an ice-bath. After the reaction was complete, it was evaporated in vacuo. To a solution of this residue in water (150 mL) was added 2N HCl (1 mL). After stirring 1 h, the reaction mixture was filtered and dried under high vacuum to give 3,5-difluorobenzenesulfonamide as a light brown solid (19.9 g, 88%). 1H NMR (400 MHz, CDCl3) δ 7.49-7.44 (m, 2H), 7.04-6.99 (m, 2H).

Workup

  1. customit was evaporated in vacuo
  2. additionTo a solution of this residue in water (150 mL) was added 2N HCl (1 mL)
  3. filtrationthe reaction mixture was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-41a2ed1b02ef47148905575ab7720070
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Linked notes

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