Cyclohexene oxide → 2-(2-Nitro-1H-imidazol-1-yl)cyclohexan-1-ol

HRID 1463042Notes

Reaction equation

HRID 1463042 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[CH:9]12[O:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]2.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 107012-NitroimidazoleHCID 11430Potassium Carbonate

Product 1

HCID 155918472-(2-Nitro-1H-imidazol-1-yl)cyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.565 g (5 mmole) of 2-nitroimidazole, 50 ml of ethanol, 5.0 ml of cyclohexene oxide, and 0.25 g of potassium carbonate was refluxed with stirring under nitrogen for 16 hr. The resulting yellow solution was evaporated and the residue dissolved in 100 ml of chloroform and filtered. The filtrate was evaporated and the residue purified by preparative TLC with ethyl acetate: benzene (2:1) as eluant to provide 0.359 g (34.0%). It was recrystallized from ethyl acetate-ether, mp 141° C.

Workup

  1. temperaturewas refluxed
  2. customThe resulting yellow solution was evaporated
  3. dissolutionthe residue dissolved in 100 ml of chloroform
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue purified by preparative TLC with ethyl acetate: benzene (2:1) as eluant
  7. customto provide 0.359 g (34.0%)
  8. customIt was recrystallized from ethyl acetate-ether, mp 141° C.

Sources & evidence

ORD record
ord-3730639e8c89457aa04a9a00be9f2fc6
Source dataset
uspto-grants-1984_07
Patent number
US04462992

Reaction notes

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