Ethyl Acetate → HCID 22930226, compound

HRID 968808Notes

Reaction equation

HRID 968808 reaction equation
[K].[N+:2]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)([O-:4])=[O:3].CS(O[CH2:15][CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])(=O)=O.C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>C(#N)C.O>[CH2:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH2:19][N:6]1[CH:7]=[CH:8][N:9]=[C:5]1[N+:2]([O-:4])=[O:3])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2855718-Crown-6HCID 22930225HCID 22930225, compoundHCID 69011836HCID 69011836, compound

Product 1

HCID 22930226HCID 22930226, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-nitro-1H-imidazole potassium salt (300 mg, 2.0 mmol), 3-ethylpentyl methanesulfonate (463 mg, 2.4 mmol) and 18-crown-6 (1.1 g, 4.2 mmol) in acetonitrile (10 ml) was heated at 80° C. for 6 hours. After cooling to room temperature, ethyl acetate and water were added and the organic layer was separated off. After washing with water and brine, drying was performed with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (370 mg) as a colorless oil.

Workup

  1. customthe organic layer was separated off
  2. washAfter washing with water and brine
  3. customdrying
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-53ae026ae42e4a118d80df3071bacb51
Source dataset
uspto-grants-2007_12
Patent number
US07304083B2

Reaction notes

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