HCID 66994844, compound → HCID 66995303, compound

HRID 1806133Notes

Reaction equation

HRID 1806133 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7][C:8]1[C:9]([N+:14]([O-])=O)=[N:10][CH:11]=[CH:12][CH:13]=1>C(O)(=O)C.[Zn]>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7][C:8]1[C:9]([NH2:14])=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 66994844HCID 66994844, compound

Product 1

HCID 66995303HCID 66995303, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

3-(1-methyl-1H-imidazol-2-ylthio)-2-nitropyridine (prepared according to the procedure of Example 359 (2.2 g, 9.3 mmol) was dissolved in acetic acid (30 mL) and cooled in a water bath. Zn dust (<10 micron, 3.0 g, 47 mmol) was slowly added in portions and the reaction stirred at ambient temperature for 30 minutes. The solution was filtered through celite (rinsing with dichloromethane) and the filtrate was concentrated. The solution was neutralized with NH4OH solution and extracted with EtOAc. The organic layer was dried and concentrated to provide the title compound (1.8 g, 94% yield) as a dark brown solid.

Workup

  1. temperaturecooled in a water bath
  2. filtrationThe solution was filtered through celite (rinsing with dichloromethane)
  3. concentrationthe filtrate was concentrated
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10424cd12fa84dcfbd35526be171f603
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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