Methanol → 2-(4-Fluoroanilino)-4-((phenylthio)methyl)benzoic acid

HRID 2191690Notes

Reaction equation

HRID 2191690 reaction equation
[OH-].[Na+].CO.[F:5][C:6]1[CH:30]=[CH:29][C:9]([NH:10][C:11]2[CH:20]=[C:19]([CH2:21][S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=1>O1CCCC1>[F:5][C:6]1[CH:30]=[CH:29][C:9]([NH:10][C:11]2[CH:20]=[C:19]([CH2:21][S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57667962Methyl 2-(4-fluoroanilino)-4-((phenylthio)methyl)benzoate

Product 1

HCID 576678622-(4-Fluoroanilino)-4-((phenylthio)methyl)benzoic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 mol/L Sodium hydroxide aqueous solution 2.0 mL was added to a mixed solution of methanol 2.4 mL and tetrahydrofuran 2.4 mL of methyl 2-(4-fluoroanilino)-4-((phenylthio)methyl)benzoate 0.48 g, and it was stirred at room temperature for 17 hours. The solvent was removed under reduced pressure, ethyl acetate and water were added to it, and it was adjusted to pH4.0 with 1.0 mol/L hydrochloric acid. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, and solid matter was filtrated to give 2-(4-fluoroanilino)-4-((phenylthio)methyl)benzoic acid 0.40 g of pale yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure, ethyl acetate and water
  2. additionwere added to it, and it
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure
  6. additionHexane and diisopropyl ether were added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-86fb27abc41547c6bc2912ea0ae66c1a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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