Sodium hydride → HCID 23081472, compound

HRID 856358Notes

Reaction equation

HRID 856358 reaction equation
Cl[C:2]1[N:3]([CH2:10][C:11]2([CH3:30])[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:18]=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:20]=[CH:21][C:22]=3[OH:23])[CH2:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>CN(C=O)C>[CH3:30][C:11]1([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:20]=[CH:21][C:22]=3[O:23][C:14]2=[O:16])[O:15][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23081423HCID 23081423, compound

Product 1

HCID 23081472HCID 23081472, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(2-chloro-4-nitroimidazol-1-ylmethyl)-3-(4-hydroxybiphenyl-3-yl)-5-methyloxazolidin-2-one prepared in Example 548 (1.23 g, 2.88 mmol), sodium hydride (127 mg, 3.16 mmol) and DMF (10 ml) was stirred at 100° C. for 4 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, and the solution was extracted with methylene chloride. The organic phase was washed with water and a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-5-phenyl-3H-benzoxazol-2-one (172 mg, yield 15%) as a yellowish brown powder.

Workup

  1. customto return to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue, water was added
  4. extractionthe solution was extracted with methylene chloride
  5. washThe organic phase was washed with water
  6. dry with materiala saturated saline solution, dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-9e131f5a9cdd492aa8f0e789ad0174d3
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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