Sulfuric Acid → 3-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

HRID 534058Notes

Reaction equation

HRID 534058 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:12]([O:13][C:14]2[C:15]([C:27]#[N:28])=[N:16][CH:17]=[C:18]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:19]=2)=[C:11]([CH3:29])[CH:10]=[CH:9][N:8]=1.[OH-:30].[Na+]>>[CH3:6][C:7]1[C:12]([O:13][C:14]2[C:15]([C:27]([NH2:28])=[O:30])=[N:16][CH:17]=[C:18]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:19]=2)=[C:11]([CH3:29])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674858013-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile

Product 1

HCID 674862983-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamideYield 94.4%

Procedure

Concentrated sulfuric acid (8 mL) was added to 3-(2,4-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (2.03 g, 6.07 mmol). The reaction was stirred overnight, then poured onto ice (100 g), cooled in an ice bath and made basic to pH 10 with 50% NaOH. The reaction was extracted with ethyl acetate, washed with brine, dried (MgSO4), and concentrated to afford 3-(2,4-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (2.02 g, 5.73 mmol, 94.4% yield) as a white solid.

Workup

  1. additionpoured onto ice (100 g)
  2. temperaturecooled in an ice bath
  3. extractionThe reaction was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a911116c75c44cf8aa7d85914bf52a3
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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