Benzyl Chloride → HCID 22632373, compound

HRID 2417547Notes

Reaction equation

HRID 2417547 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([OH:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[C:16](=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO.CN(C=O)C.C(OCC)(=O)C>[CH2:22]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([C:9]([O:11][CH3:16])=[O:10])=[N:6]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 178524956HCID 178524956, compound

Product 1

HCID 22632373HCID 22632373, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 g (63.7 mmol) of 4-nitro-3-pyrazolecarboxylic acid was dissolved in 100 ml of methanol. 5.7 ml (76.4 mmol) of thionyl chloride was added dropwise to the obtained solution under cooling with ice. The temperature was elevated to room temperature and the obtained mixture was stirred for 2 days. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated. The obtained crude product was dissolved in 150 ml of DMF. 9.5 g (68.8 mmol) of potassium carbonate and 7.5 ml (65.0 mmol) of benzyl chloride were added to the obtained solution, and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customwas elevated to room temperature
  3. customAfter the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated
  4. customThe obtained crude product
  5. stirringwere stirred at room temperature overnight
  6. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-0d3ebd03ed194ab5a282b89c2c2ad885
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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