Thionyl Chloride → 4-(chloromethyl)-1-phenyl-1H-pyrazole

HRID 914452Notes

Reaction equation

HRID 914452 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([CH2:12]O)[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:16][CH2:12][C:10]1[CH:9]=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 822983(1-phenyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 21211624-(chloromethyl)-1-phenyl-1H-pyrazoleYield 106.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(1-Phenyl-1H-pyrazol-4-yl)methanol (6.3 g) synthesized in Reference Example 17 was dissolved in dichloromethane (100 mL) and, after ice-cooling, thionyl chloride (5.59 g) was added thereto, and the mixture was stirred at 0° C. for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (7.4 g) as a white solid.

Workup

  1. temperatureafter ice-cooling
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-14b05bdfa4cf48ae9e5231de0184d5cc
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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