4-Amino-2,6-dichlorophenol → 2-Chloro-N-(3,5-dichloro-4-hydroxy-phenyl)-4-trifluoromethyl-benzenesulfonamide

HRID 1370521Notes

Reaction equation

HRID 1370521 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[CH:14][C:13]=1[S:22]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 800374-Amino-2,6-dichlorophenolHCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 185115142-Chloro-N-(3,5-dichloro-4-hydroxy-phenyl)-4-trifluoromethyl-benzenesulfonamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-2,6-dichlorophenol (Aldrich, 5.9 g, 33 mmol) in 30 mL of THF was added 2-chloro-4-trifluoromethylbenzenesulfonyl chloride (4.19 g, 15 mmol). The mixture was stirred overnight. The reaction mixture was filtered and washed with EtOAc. The filtrate was washed with 2N HCl, twice with a brine solution, dried over Na2SO4 and concentrated. The residue was purified by chromatography (20%-25% EtOAc/hexanes) to give 5.7 g (90%) of product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with EtOAc
  3. washThe filtrate was washed with 2N HCl, twice with a brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (20%-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a62dbd02728e4d29bc42786f1f8028f7
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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