Sodium hydride → HCID 67190155, compound

HRID 546032Notes

Reaction equation

HRID 546032 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1>CN(C)C=O>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178526745HCID 178526745, compound

Product 1

HCID 67190155HCID 67190155, compoundYield 82%

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, 4-methyoxybenzylchloride (312 μL, 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 1-(4-methoxy-benzyl)-3-nitro-1H-pyrazole (337 mg, 82%) as a white solid: H1-NMR (400 MHz, CDCl3) δ: 3.77 (3H, s), 5.27 (2H, s), 6.83 (1H, d, J=2.3 Hz), 6.86 (2H, d, J=8.6 Hz), 7.22 (2H, d, J=8.5 Hz), 7.35 (1H, d, J=2.3 Hz).

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-c51108159c344c7e83f36c0a776e4aa3
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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