2-Nitroimidazole → 1H-Imidazole, 1-(3-methyl-2-butenyl)-2-nitro-

HRID 609515Notes

Reaction equation

HRID 609515 reaction equation
[Na].[N+:2]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)([O-:4])=[O:3].Br[CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14]>C(#N)C>[CH3:14][C:13]([CH3:15])=[CH:12][CH2:11][N:6]1[CH:7]=[CH:8][N:9]=[C:5]1[N+:2]([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 700922-Butene, 1-bromo-3-methyl-HCID 5360545Sodium

Product 1

HCID 113443651H-Imidazole, 1-(3-methyl-2-butenyl)-2-nitro-Yield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the sodium salt of 2-nitroimidazole prepared above was added acetonitrile (50 ml), 15-crown-5-ether (3.5 ml, 14.3 mmol) and 4-bromo-2-methyl-2-butene (2 ml; 17.4 mmol). The mixture was stirred at RT for ca 16 h. and then the solvent was removed to leave a crude semi-solid which was purified by column chromatography on silica. The intermediate product, 1-(3-methyl-2-butenyl)-2-nitroimidazole (80% yield) was eluted using a mixture of petroleum ether (40-60)/ethyl acetate (ratio 4:1 respectively).

Workup

  1. customthe solvent was removed
  2. customto leave a crude semi-solid which
  3. customwas purified by column chromatography on silica

Sources & evidence

ORD record
ord-728138628f044e39bf42b12ad90f8c95
Source dataset
uspto-grants-1999_12
Patent number
US05997843

Reaction notes

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