Thionyl Chloride → HCID 22030137, compound

HRID 968620Notes

Reaction equation

HRID 968620 reaction equation
[N+:1]([C:4]1[C:9](=O)[NH:8][CH:7]=[C:6]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:23])=O>CN(C=O)C>[Cl:23][C:9]1[N:8]=[CH:7][C:6]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22030083HCID 22030083, compound

Product 1

HCID 22030137HCID 22030137, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat a solution of 5′-nitro-3-trifluoromethyl-1′H-[2,3′]bipyridinyl-6′-one (25 g, 0.088 mol), thionyl chloride (300 mL) and DMF (3 mL) to reflux for 4 hours. Remove the volatiles by rotary evaporation and partition the residue between ethyl acetate (350 mL) and saturated sodium bicarbonate solution (250 mL). Extract the aqueous layer with further ethyl acetate (250 mL) and wash the combined organics with brine (250 mL). Dry (MgSO4) and concentrate under reduced pressure to give the title compound (25 g, 93%) as a yellow oil.

Workup

  1. temperatureto reflux for 4 hours
  2. customRemove the volatiles
  3. customby rotary evaporation
  4. custompartition the residue between ethyl acetate (350 mL) and saturated sodium bicarbonate solution (250 mL)
  5. extractionExtract the aqueous layer with further ethyl acetate (250 mL)
  6. washwash the combined organics with brine (250 mL)
  7. dry with materialDry (MgSO4)
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1e92cbde95014a5b9c0a1bea95a649da
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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