Sodium Hydroxide → 4-((3-(Trifluoromethoxy)phenyl)sulfonyl)aniline

HRID 1754113Notes

Reaction equation

HRID 1754113 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)C)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+]>CCO>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70978998N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acetamide

Product 1

HCID 891567704-((3-(Trifluoromethoxy)phenyl)sulfonyl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acetamide (104 mg, 0.29 mmol) in EtOH (8 mL) is added NaOH (10 M in water, 0.6 mL, 6 mmol). The mixture is heated at 80° C. for 4 h and the solvent is evaporated. The residue is partitioned between EtOAc (15 mL) and brine (10 mL) and the layers are separated. The aqueous layer is extracted with EtOAc (10 mL) and the combined extracts are dried (Na2SO4) and evaporated. The white solid obtained (86 mg, 93%) is used to the next step without further purification.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between EtOAc (15 mL) and brine (10 mL)
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc (10 mL)
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. customevaporated
  7. customThe white solid obtained (86 mg, 93%)
  8. customis used to the next step without further purification

Sources & evidence

ORD record
ord-c28c4b314c3f439fbf8aa6f320d4b608
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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