Sulfuric Acid → HCID 67486463, compound

HRID 1523606Notes

Reaction equation

HRID 1523606 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:8]([S:13][C:14]2[CH:15]=[C:16]([O:22][C:23]3[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]([C:20]#[N:21])=[N:18][CH:19]=2)=[N:9][CH:10]=[CH:11][CH:12]=1.[OH-:30].[Na+]>>[CH3:6][C:7]1[C:8]([S:13][C:14]2[CH:15]=[C:16]([O:22][C:23]3[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]([C:20]([NH2:21])=[O:30])=[N:18][CH:19]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67487618HCID 67487618, compound

Product 1

HCID 67486463HCID 67486463, compoundYield 94.9%

Procedure

Concentrated sulfuric acid (8 mL) was added to 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinonitrile (1.40 g, 4.19 mmol). The reaction was stirred over the weekend, then poured onto ice (100 g), cooled in an ice bath and made basic to pH 10 with 50% NaOH. The reaction mixture was extracted with ethyl acetate, washed with brine, dried (MgSO4), and concentrated to afford 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinamide (1.40 g, 3.97 mmol, 94.9% yield) as a colorless oil which became a white crystalline solid overnight under vacuo.

Workup

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

Sources & evidence

ORD record
ord-001e29c999d14f3cadfa67c137faf461
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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