Sodium hydride → HCID 7172345, compound

HRID 546035Notes

Reaction equation

HRID 546035 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15]Br>CN(C)C=O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 178526745HCID 178526745, compound

Product 1

HCID 7172345HCID 7172345, compoundYield 77%

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, 3,4-dichlorobenzylbromide (550 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 1-(3,4-dichloro-benzyl)-3-nitro-1H-pyrazole (369 mg, 77%) as a white solid: H1-NMR (400 MHz, CDCl3) δ: 5.32 (2H, s), 6.92 (1H, d, J=2.3 Hz), 7.12 (1H, m), 7.36 (1H, d, J=2.2 Hz), 7.44 (2H, 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-6e91ad8dc5b44d77bedbbbd4ebe2f5bb
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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