Sodium hydride → HCID 10481193, compound

HRID 856214Notes

Reaction equation

HRID 856214 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:27]1[N:28]([CH2:35][C:36]2([CH3:39])[CH2:38][O:37]2)[CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[N:31]=1>CN(C=O)C>[CH3:38][C:36]1([CH2:39][O:21][C:18]2[CH:19]=[CH:20][C:15]([N:12]3[CH2:13][CH2:14][N:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:22])[F:23])=[CH:8][CH:7]=4)[CH2:10][CH2:11]3)=[CH:16][CH:17]=2)[O:37][C:27]2=[N:31][C:30]([N+:32]([O-:34])=[O:33])=[CH:29][N:28]2[CH2:35]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 159655232-Chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 69479586HCID 69479586, compound

Product 1

HCID 10481193HCID 10481193, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[4-(4-Trifluoromethylphenyl)piperazin-1-yl]phenol (296 mg, 0.92 mmol) was dissolved in DMF (10 ml). To the solution, sodium hydride (44 mg, 1.1 mmol) was added at room temperature, and the solution was stirred for 20 minutes at 80° C. To the solution, 2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 6 (200 mg, 0.92 mmol) was added with cooling on ice-bath, and the solution was stirred for further 20 minutes at 80° C. To the reaction mixture, ice-water was added, and the solution was stirred vigorously. The precipitates were filtered off, washed with water and dissolved in methylene chloride. The solution 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/ethyl acetate to afford 2-methyl-6-nitro-2-{4-[4-(4-trifluoromethylphenyl)piperazin-1-yl]phenoxymethyl}-2,3-dihydroimidazo[2,1-b]oxazole (178 mg, yield 38%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringthe solution was stirred for further 20 minutes at 80° C
  3. stirringthe solution was stirred vigorously
  4. filtrationThe precipitates were filtered off
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. washThe solution was washed with a saturated saline solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe resulting filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1)
  12. customcrystallized from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-425392fc4da44360926655ec37734904
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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