Sodium Hydroxide → 3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

HRID 534026Notes

Reaction equation

HRID 534026 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([C:23]#[N:24])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[OH-:25].[Na+]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([C:23]([NH2:24])=[O:25])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67485570HCID 67485570, compound

Product 1

HCID 674861443-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (1.4 g, 4.19 mmol) was stirred in concentrated sulfuric acid (10 mL) overnight at ambient temperature. Ice (100 g) was added and the solution was neutralized using 4M NaOH. Ice was added as necessary to maintain the temperature below 20° C. The product was extracted into ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (1.5 g, 4.2 mmol).

Workup

  1. additionIce was added as necessary
  2. temperatureto maintain the temperature below 20° C
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2cd3ad03df024236b6783eac7e125561
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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