Cesium carbonate → 4-Nitro-1-(oxetan-3-yl)-1H-imidazole

HRID 593057Notes

Reaction equation

HRID 593057 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].I[CH:10]1[CH2:13][O:12][CH2:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:10]2[CH2:13][O:12][CH2:11]2)[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 133566863-IodooxetaneHCID 178526856HCID 178526856, compound

Product 1

HCID 866845194-Nitro-1-(oxetan-3-yl)-1H-imidazoleYield 33.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A sealed tube was charged with 4-nitro-1H-imidazole (500 mg, 4.42 mmol), 3-iodooxetane (920 mg, 5.0 mmol), Cs2CO3 (2.90 g, 8.84 mmol), and dioxane (12 mL). The sealed tube was heated at 120° C. for 16 h. It was then cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 285a as a white solid (250 mg, 33%). MS-ESI: [M+H]+ 170.2.

Workup

  1. temperatureIt was then cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography
  5. washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-749351565f5546f7af33f2c572bf3141
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

Loading…