Sodium hydride → HCID 69482067, compound

HRID 856308Notes

Reaction equation

HRID 856308 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:15]1[N:16]([CH2:23][C@@H:24]2[CH2:26][O:25]2)[CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[N:19]=1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:26][C@@H:24]3[O:25][C:15]4=[N:19][C:18]([N+:20]([O-:22])=[O:21])=[CH:17][N:16]4[CH2:23]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 974781-(4-Chlorophenyl)piperazineHCID 86604801HCID 86604801, compound

Product 1

HCID 69482067HCID 69482067, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, a mixture of 1-(4-chlorophenyl)-piperazine obtained, (R)-2-chloro-1-(oxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 9 (763 mg, 3.75 mmol) and DMF (5 ml) was stirred at 70° C. for 6 hours. To the solution, sodium hydride (219 mg, 5.48 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 2 hours. To the reaction mixture, ice-water was added, and precipitates were filtered off. The resulting solids were recrystallized from acetone/water to afford (S)-2-[4-(4-chlorophenyl)piperazin-1-ylmethyl]-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (250 mg, yield 18%) as a light yellow powder.

Workup

  1. customobtained
  2. temperaturewith cooling on ice-bath
  3. customprecipitates
  4. filtrationwere filtered off
  5. customThe resulting solids were recrystallized from acetone/water

Sources & evidence

ORD record
ord-4122b60a971548e093fb5f83ca0b3a12
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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