Thionyl Chloride → 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole

HRID 349927Notes

Reaction equation

HRID 349927 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([CH2:23]O)[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([CH2:23][Cl:3])[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23025093(1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 230250441-benzyl-4-chloromethyl-5-phenyl-1H-pyrazoleYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (4.35 g) was added to a solution of (1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol (8.06 g) in toluene (100 ml) dropwise at 0° C., and the mixture was stirred at room temperature for one hour and then refluxed for ten minutes. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole (8.31 g, yield: 96%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. temperaturerefluxed for ten minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5da7c8d0132c42a28530ec8bb0aaa86b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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