Hydrochloric Acid → 4-(Benzylthio)-2-(4-fluoroanilino)benzoic acid

HRID 2191688Notes

Reaction equation

HRID 2191688 reaction equation
[OH-].[Na+].CC(O)C.[CH2:7]([S:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(OCC)(=O)C>[CH2:7]([S:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 57667795Methyl 4-(benzylthio)-2-(4-fluoroanilino)benzoate

Product 1

HCID 576679824-(Benzylthio)-2-(4-fluoroanilino)benzoic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10% Sodium hydroxide aqueous solution 1.0 mL was added to a suspension of 2-propanol 4.0 mL of methyl 4-(benzylthio)-2-(4-fluoroanilino)benzoate 0.36 g at room temperature, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, 1.0 mol/L hydrochloric acid and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue, solid matter was filtrated to give 4-(benzylthio)-2-(4-fluoroanilino)benzoic acid 0.30 g of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 2 hours
  3. customThe organic layer was separated
  4. customthe solvent was removed under reduced pressure
  5. additionDiisopropyl ether and hexane were added to the obtained residue, solid matter
  6. filtrationwas filtrated

Sources & evidence

ORD record
ord-e2f396ed49f248b0aac87119456c1884
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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