Sodium Hydroxide → HCID 5111670, compound

HRID 395810Notes

Reaction equation

HRID 395810 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.CO>O>[N:1]1[CH:2]=[CH:3][C:4]([S:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18174558HCID 18174558, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 5111670HCID 5111670, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-(4-pyridylthio)benzoate (400 mg, 1.54 mmol) and 5 N aqueous sodium hydroxide (2 mL) in 1:1 tetrahydrofuran/methanol (2 mL) was stirred at room temperature for 18 h. The mixture was diluted with water and washed with diethyl ether. The aqueous layer was acidified to pH 6 with concentrated hydrochloric acid. The resulting precipitate was collected via vacuum filtration to provide 280 mg (78%) of the title compound as a pale yellow solid.

Workup

  1. washwashed with diethyl ether
  2. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-714d3310d2514a7bb915d80ccdef7dae
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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