Sodium hydride → 2-(2-Methoxymethoxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856162Notes

Reaction equation

HRID 856162 reaction equation
[H-].[Na+].Cl[C:4]1[N:5]([CH2:12][CH:13]([OH:20])[CH2:14][CH2:15][O:16][CH2:17][O:18][CH3:19])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1>O1CCOCC1>[CH3:19][O:18][CH2:17][O:16][CH2:15][CH2:14][CH:13]1[O:20][C:4]2=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][N:5]2[CH2:12]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 230814622-Chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazole

Product 1

HCID 230815542-(2-Methoxymethoxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (1.33 g, 33.23 mmol) was added to a solution of 2-chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazole prepared in Example 23 (8.45 g, 30.21 mmol) in 1,4-dioxane (100 ml) with cooling on ice-bath followed by stirring under reflux for 40 hours. The reaction mixture was concentrated under reduced pressure, and cooled on ice-bath. Water was added to the residue, and the resulting mixture was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and crystallized from methylene chloride-diisopropyl ether to afford 2-(2-methoxymethoxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (3.4 g, yield 47%) as a light yellow powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. temperatureunder reflux for 40 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. temperaturecooled on ice-bath
  5. additionWater was added to the residue
  6. extractionthe resulting mixture was extracted with methylene chloride
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  10. customcrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-28853b5d256043a0bbb6a3221e2a809b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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