HCID 66994844, compound → HCID 66995303, compound

HRID 335207Notes

Reaction equation

HRID 335207 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-992268d841a34830a0e710f24ac6d6b4
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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