Thionyl Chloride → HCID 86683873, compound

HRID 2406745Notes

Reaction equation

HRID 2406745 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-9dd901bad09343f6871136006cf4a19b
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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