Pyrazole → 3-[2-(1H-1-pyrazolyl)acetyl]benzonitrile

HRID 2184909Notes

Reaction equation

HRID 2184909 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:4].[NH:13]1[CH:17]=[CH:16][CH:15]=[N:14]1.C(N(CC)CC)C>ClCCl>[N:13]1([CH2:2][C:3]([C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[C:8]#[N:9])=[O:4])[CH:17]=[CH:16][CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 8471TriethylamineHCID 27358673-(2-Bromoacetyl)benzonitrile

Product 1

HCID 224583253-[2-(1H-1-pyrazolyl)acetyl]benzonitrileYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(2-bromoacetyl)benzonitrile (500 mg, 2.23 mmol) in 5 ml dichloromethane was added pyrazole (304 mg, 4.46 mmol) and triethylamine (0.31 ml, 2.23 mmol). Reaction was stirred at room temperature over night. Reaction was then diluted with 20 ml dichloromethane, washed with 2×25 ml water, 2×25 ml 1N HCl, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane to give 3-[2-(1H-1-pyrazolyl)acetyl]benzonitrile (330 mg, 70%) as a clear oil after drying. ES-MS (M+H+): 212.05

Workup

  1. customReaction
  2. customReaction
  3. washwashed with 2×25 ml water, 2×25 ml 1N HCl
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customCrude residue was chromatographed on silica gel using 2.5% EtOAc in hexane

Sources & evidence

ORD record
ord-4592cdd310cf42aa85d75731ccd8b0f3
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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