Water → HCID 67485792, compound

HRID 1809649Notes

Reaction equation

HRID 1809649 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[NH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=[S:24].[H-].[Na+].O>CN(C=O)C>[CH3:17][C:12]1[C:11]([O:10][C:4]2[C:5]([C:8]#[N:9])=[N:6][CH:7]=[C:2]([S:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[CH:3]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27236982-MercaptopyridineHCID 67485726HCID 67485726, compound

Product 1

HCID 67485792HCID 67485792, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (56.9 g, 196 mmol) and pyridine-2(1H)-thione (22.9 g, 206 mmol) were dissolved in DMF (400 mL) and cooled to 0° C. NaH (4.94 g, 206 mmol) was added portionwise and warmed to ambient temperature. The reaction was stirred for 18 hours and then poured into 2.5 L of water and stirred for 30 minutes The solids were filtered to provide 3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (60.8 g, 190 mmol, 96.8% yield).

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for 30 minutes The solids
  3. filtrationwere filtered

Sources & evidence

ORD record
ord-55137a0891bd40749f6c3030be9f5094
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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