Sodium Hydroxide → HCID 67997122, compound

HRID 45782Notes

Reaction equation

HRID 45782 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 67997039HCID 67997039, compound

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-2db41edb870f4ea58a035b6915f97e3b
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

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