4-Nitro-2,2'-bipyridine-N-oxide → HCID 59201292, compound

HRID 925293Notes

Reaction equation

HRID 925293 reaction equation
[CH3:1][S-:2].[Na+].[N+]([C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N+:10]([O-:13])=[CH:11][CH:12]=1)([O-])=O>CN(C)C=O>[CH3:1][S:2][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N+:10]([O-:13])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 33312824-Nitro-2,2'-bipyridine-N-oxideHCID 4378561Sodium methanethiolate

Product 1

HCID 59201292HCID 59201292, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium thiomethoxide (1.06 g, 15.2 mmol) was added at 25° C. to 4-Nitro-[2,2′]bipyridinyl 1-oxide (3.0 g, 13.8 mmol) in dimethyl formamide (15 mL) and stirred for 2 hours at 50° C. The reaction mixture was added into ice (200 g) under vigorous stirring, the solid formed was filtered and washed with water (100 mL) and ether (100 mL), the filtrate was concentrated, diluted with water, extracted with dichloromethane (3×100 mL), dried with anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (0-100% Ethyl acetate in Hexane) to afford 4-methylsulfanyl-[2,2′]bipyridinyl 1-oxide as a white solid (650.0 mg, 22%).

Workup

  1. customthe solid formed
  2. filtrationwas filtered
  3. washwashed with water (100 mL) and ether (100 mL)
  4. concentrationthe filtrate was concentrated
  5. additiondiluted with water
  6. extractionextracted with dichloromethane (3×100 mL)
  7. dry with materialdried with anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude was purified by column chromatography on silica gel (0-100% Ethyl acetate in Hexane)

Sources & evidence

ORD record
ord-3f1b4a33091b4491b39299e536c7653b
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

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