p-Toluenesulfonic acid → 2-Nitro-1-(oxolan-2-yl)-1H-imidazole

HRID 1463039Notes

Reaction equation

HRID 1463039 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[O:9]1[CH:13]=[CH:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[O:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 107012-NitroimidazoleHCID 709342,3-Dihydrofuran

Product 1

HCID 155918442-Nitro-1-(oxolan-2-yl)-1H-imidazoleYield 75.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.338 g (3.0 mmol) of 2-nitroimidazole and 0.7 ml of 2,3-dihydrofuran in 35 ml of acetonitrile was stirred at 35°-45° C. in the presence of 5 mg of p-toluenesulfonic acid for 2 hr. under nitrogen and then evaporated. The residue was dissolved in chloroform, filtered, and evaporated to yield a syrup which was purified by preparative TLC with ethyl acetate-benzene (1:1) to provide 0.41 g (75.3%) of the title compound, mp 91° C.

Workup

  1. customunder nitrogen and then evaporated
  2. dissolutionThe residue was dissolved in chloroform
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a syrup which
  6. customwas purified by preparative TLC with ethyl acetate-benzene (1:1)

Sources & evidence

ORD record
ord-ccc72c12bb124d8e85c79d4cd69fa90c
Source dataset
uspto-grants-1984_07
Patent number
US04462992

Reaction notes

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