Sulfuric Acid → 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide

HRID 1523659Notes

Reaction equation

HRID 1523659 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:16][C:17]2[C:18]([CH3:24])=[N:19][N:20]([CH3:23])[C:21]=2[CH3:22])[C:11]([C:14]#[N:15])=[N:12][CH:13]=1.S(=O)(=O)(O)[OH:26].[OH-].[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:16][C:17]2[C:18]([CH3:24])=[N:19][N:20]([CH3:23])[C:21]=2[CH3:22])[C:11]([C:14]([NH2:15])=[O:26])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674864015-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

Product 1

HCID 674856415-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamideYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (35.19 g, 88.1 mmol), and sulfuric acid (227.3 g, 2317 mmol) and stirred at ambient temperature overnight. Water (100 mL) was slowly added to the reaction which was cooled in an ice bath, then ice (150 g) was added. 40% NaOH was slowly added until the pH was about 12. The mixture was extracted ethyl acetate (750 mL×2), and dichloromethane (500 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo to afford 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide (27.69 g, 77.9 mmol, 89% yield).

Workup

  1. temperaturewas cooled in an ice bath
  2. extractionThe mixture was extracted ethyl acetate (750 mL×2), and dichloromethane (500 mL)
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a9d66b06ea5401cbfca4d08481ba356
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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