Sodium Hydroxide → 4-(4-Methoxyphenyl)sulfonylaniline

HRID 1754109Notes

Reaction equation

HRID 1754109 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70978553N-(4-((4-methoxyphenyl)sulfonyl)phenyl)acetamide

Product 1

HCID 5166674-(4-Methoxyphenyl)sulfonylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(4-((4-methoxyphenyl)sulfonyl)phenyl)acetamide (111 mg, 0.36 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 (76 mg, 80%) 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 (76 mg, 80%)
  8. customis used to the next step without further purification

Sources & evidence

ORD record
ord-c9df4bdace9147c9b87ab9e07438a8dd
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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