Benzyl Bromide → 1-Benzyl-4-nitro-1H-pyrazole

HRID 2063656Notes

Reaction equation

HRID 2063656 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C.O>[CH2:11]([N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 163764-nitro-1H-pyrazoleHCID 24758Sodium hydride

Product 1

HCID 9736451-Benzyl-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitro-1H-pyrazole (283 mg, 2.5 mmol) in dry DMF (5 ml) under an argon atmosphere was added NaH (120 mg, 2.75 mmol) in small portions at 0° C. The reaction mixture was stirred at rt for 1 hour, cooled again to 0° C. before benzyl bromide (300 μl, 2.5 mmol) was added and stirred at rt for 12 h. The mixture was diluted with water, extracted with ethyl acetate and the product was purified by chromatography on silica gel using heptane/ethyl acetate as eluent. The title compound was obtained as light yellow oil (484 mg, 95%). MS ISP (m/e): 226.3 (100) [(M+Na)+].

Workup

  1. additionwas added
  2. stirringstirred at rt for 12 h
  3. extractionextracted with ethyl acetate
  4. customthe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c38ab065b74444d18c9b5a2c1e7e7b9e
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

Loading…