Sodium Hydroxide → HCID 67997122, compound

HRID 470390Notes

Reaction equation

HRID 470390 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:14]([S:19][CH2:20][C:21]([O:23]C)=[O:22])=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:14]([S:19][CH2:20][C:21]([OH:23])=[O:22])=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67997039Methyl 2-(3-(4-cyanonaphthalen-1-yl)pyrazin-2-ylthio)acetate

Product 1

HCID 67997122HCID 67997122, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(4-cyanonaphthalen-1-yl)pyrazin-2-ylthio)acetate (0.125 g, 0.37 mmol), aqueous sodium hydroxide solution (1M, 0.5 mL) and methanol (1 mL) was stirred at room temperature for 12 hours. Methanol was removed and the mixture washed with water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to dryness. Solid residue was recrystallized from ethyl acetate and hexanes to yield 2-(3-(4-cyanonaphthalen-1-yl)pyrazin-2-ylthio)acetic acid (0.102 g, 86%).

Workup

  1. customMethanol was removed
  2. washthe mixture washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customSolid residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-f41c7e0578384daf92f08ff46313cef9
Source dataset
uspto-grants-2014_01
Patent number
US08629278B2

Reaction notes

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