Thionyl Chloride → HCID 86683873, compound

HRID 1620097Notes

Reaction equation

HRID 1620097 reaction equation
S(Cl)([Cl:3])=O.O[C:6]1[C:11]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:10][C:9]([N+:17]([O-:19])=[O:18])=[CH:8][N:7]=1>CN(C=O)C>[Cl:3][C:6]1[C:11]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:10][C:9]([N+:17]([O-:19])=[O:18])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178526841HCID 178526841, compound

Product 1

HCID 86683873HCID 86683873, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (6 ml) and DMF (0.1 ml) were added to 2-hydroxy-5-nitro-3-(1H-pyrazol-1-yl)pyridine (1.37 g), followed by stirring at 80° C. for 2.5 hours. The reaction solution was adjusted to room temperature and slowly added to ice water, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1 to 3:1), and a yellow solid of 2-chloro-5-nitro-3-(1H-pyrazol-1-yl)pyridine (0.12 g) was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1 to 3:1)

Sources & evidence

ORD record
ord-0fbb37126e1f4e81bd95b55cf86fd255
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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