Phenethyl bromide → 3-Nitro-1-(2-phenylethyl)-1H-pyrazole

HRID 546038Notes

Reaction equation

HRID 546038 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 178526745HCID 178526745, compound

Product 1

HCID 587099233-Nitro-1-(2-phenylethyl)-1H-pyrazoleYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 200 mg, 1.77 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (92 mg, 2.30 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 20 min, (2-bromo-ethyl)-benzene (426 mg, 2.30 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride) afforded 3-nitro-1-phenethyl-1H-pyrazole (301 mg, 78%) as a white solid: H1-NMR (400 MHz, CDCl3) δ: 3.21 (3H, t, J=7.0 Hz), 4.41 (3H, t, J=6.9 Hz), 6.76 (1H, d, J=2.3 Hz), 7.07 (2H, m), 7.15 (1H, d, J=2.3 Hz), 7.27 (3H, m).

Workup

  1. stirringthe mixture was stirred for additional 20 min
  2. stirringto stir under nitrogen for an additional 2 h
  3. customThe solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-1c147fe7a87d461db527e9c574b55dd2
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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