Sodium hydride → HCID 23081136, compound

HRID 856213Notes

Reaction equation

HRID 856213 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H-].[Na+].Cl[C:16]1[N:17]([CH2:24][C:25]2([CH3:28])[CH2:27][O:26]2)[CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[N:20]=1>CN(C=O)C>[CH3:27][C:25]1([CH2:28][O:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=2)[O:26][C:16]2=[N:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][N:17]2[CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70015p-(Trifluoromethoxy)phenolHCID 159655232-Chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole

Product 1

HCID 23081136HCID 23081136, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Trifluoromethoxyphenol (198 mg, 1.11 mmol) was dissolved in DMF (5 ml). To the solution, sodium hydride (48 mg, 1.21 mmol) was added at room temperature, and the solution was stirred for 20 minutes at 80° C. To the resulting solution, 2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 6 (220 mg, 1.01 mmol) was added with cooling on ice-bath, and the solution was stirred for 15 minutes at 80° C. The reaction mixture was poured into ice-water, and the mixture was extracted with ethyl acetate. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1) and then crystallized from methylene chloride-diisopropyl ether to afford 2-methyl-6-nitro-2-(4-trifluoromethoxyphenoxymethyl)-2,3-dihydroimidazo[2,1-b]oxazole (170 mg, yield 47%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringthe solution was stirred for 15 minutes at 80° C
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with a saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1)
  9. customcrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-db0db8bbbaa548c0a6ccded0cdf4643f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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