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

HRID 1463040Notes

Reaction equation

HRID 1463040 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1>>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 107012-Nitroimidazole

Product 1

HCID 155918452-Nitro-1-(oxan-2-yl)-1H-imidazoleYield 83.7%

Procedure

A suspension of 0.113 g (1.0 mmol) of 2-nitroimidazole and 10 ml of 2,3-dihydropyran was stirred at 80° C. in the presence of 5 mg of p-toluenesulfonic acid for 1 hr. according to the procedure of Robins et al. [J. Am. Chem. Soc 83, 2574 (1961)]. The excess of 2,3-dihydropyran was removed under reduced pressure. The residue was chromatographed on silica gel by elution with ethyl acetate-benzene mixture (employing a gradient from 9:1 to 1:1) to provide 0.165 g (83.7%) of the title compound, which was recrystallized from petroleum ether, mp 50° C.

Workup

  1. customThe excess of 2,3-dihydropyran was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel by elution with ethyl acetate-benzene mixture (

Sources & evidence

ORD record
ord-397fc46811934af58f370effe98ea2f8
Source dataset
uspto-grants-1984_07
Patent number
US04462992

Reaction notes

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