Ammonium → 2-Fluoro-5-(4-methoxy-benzoyl)-benzenesulfonamide

HRID 873623Notes

Reaction equation

HRID 873623 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18](Cl)(=[O:20])=[O:19].[NH4+:22]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18]([NH2:22])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 223AmmoniumHCID 581074472-Fluoro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride

Product 1

HCID 442352782-Fluoro-5-(4-methoxy-benzoyl)-benzenesulfonamideYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluoro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride (0.45 g, 1.0 mmol) in methylene chloride is added aqueous ammonium solution (1 mL). The reaction mixture is stirred for 10 min at room temperature. The solvent is removed and the residue is redissolved in ethyl acetate and extracted with water. The organic layers are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. The residue is recrystallized with methylene chloride-hexane to give 100 mg (32% yield) of the title compound as pale yellow solid. 1H NMR (CDCl3): δ 8.40 (m, 1H), 8.05 (m, 1H), 7.80 (d, J=8 Hz, 2H), 7.32 (t, 1H), 7.00 (d, J=8 Hz, 2H), 5.15 (s, 1H), 3.90 (s, 3H). Analytics calculated for C14H12FNO4S: C, 54.36; H, 3.91; N, 4.53. Found: C, 53.89; H, 3.50; N, 4.50.

Workup

  1. customThe solvent is removed
  2. dissolutionthe residue is redissolved in ethyl acetate
  3. extractionextracted with water
  4. washThe organic layers are washed with a saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallized with methylene chloride-hexane

Sources & evidence

ORD record
ord-5ece9546d2dc454faff3b27f80ad36b4
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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