Sodium Hydroxide → HCID 64167014, compound

HRID 1422837Notes

Reaction equation

HRID 1422837 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)[CH:5]=1.[OH-].[Na+]>CO.C1COCC1.O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([S:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:18])=[O:2])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67380693HCID 67380693, compound

Product 1

HCID 64167014HCID 64167014, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 3-(5-chloro-pyridin-2-ylsulfanyl)-benzoic acid methyl ester (780 g, 2.8 mmol) and NaOH (500 mg, 12 mmol) in methanol:THF:water (1:1:1, 6 mL) was stirred at room temperature for 8 h. Solvents were evaporated. Crude mass was taken in water (40 mL), acidified to pH 4.0 and extracted with ethyl acetate. Evaporation of ethyl acetate provided 3-(5-chloro-pyridin-2-ylsulfanyl)-benzoic acid (580 mg).

Workup

  1. customSolvents were evaporated
  2. extractionextracted with ethyl acetate
  3. customEvaporation of ethyl acetate

Sources & evidence

ORD record
ord-b59cdf05c04b4ed9a82b122258fce509
Source dataset
uspto-grants-2015_01
Patent number
US08927549B2

Reaction notes

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