Dimethylformamide → HCID 18673595, compound

HRID 1635939Notes

Reaction equation

HRID 1635939 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH2:9](Br)[C:10]1[CH:18]=[CH:17][C:16]2[O:15][CH2:14][O:13][C:12]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCCCCC.C(OC(=O)C)C>[CH2:14]1[O:15][C:16]2[CH:17]=[CH:18][C:10]([CH2:9][N:7]3[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]3)=[CH:11][C:12]=2[O:13]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 64514231,3-Benzodioxole, 5-(bromomethyl)-HCID 178526856HCID 178526856, compound

Product 1

HCID 18673595HCID 18673595, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

3.39 g(30 mmol) of 4-nitroimidazole, 6.45 g(30 mmol) of piperonyl bromide and 8.28 g(60 mmol) of potassium carbonate were added to 100 ml of dimethylformamide and the resulting mixture was reacted for 6 hours. The reaction solution was concentrated by removing the solvent. The residue was dissolved in 100 ml of ethylacetate and the combined organic layer was washed twice with 100 ml of water. The organic layer was separated, concentrated and then subjected to column chromatography (eluent: hexane/ethylacetate=2/1, v/v) to give 6.17 g(1.52 mmol, Yield 83%) of the title compound.

Workup

  1. customthe resulting mixture was reacted for 6 hours
  2. concentrationThe reaction solution was concentrated
  3. customby removing the solvent
  4. dissolutionThe residue was dissolved in 100 ml of ethylacetate
  5. washthe combined organic layer was washed twice with 100 ml of water
  6. customThe organic layer was separated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29ac31a6ab024b5e8b08890acc4c09f9
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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