Potassium Carbonate → 1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

HRID 1812156Notes

Reaction equation

HRID 1812156 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>CN(C=O)C.C(Cl)Cl>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 666114661-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-nitro-1H-pyrazole (500 mg, 4.42 mmol; Bionet Research, Cornwall, UK) in DMF (5 mL) was treated with potassium carbonate (400 μL, 6.63 mmol) and 4-methoxybenzyl chloride (600 μL, 4.42 mmol). The reaction was stirred at room temperature for 2 h, then diluted with DCM (200 mL) and washed with water (4×40 mL). The organic layer was then dried (MgSO4), filtered and concentrated in vacuo to give the crude product, which was used in the next step without further purification.

Workup

  1. washwashed with water (4×40 mL)
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f11344a013b4889ba4f47204d62fe4c
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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