Imidazole → 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole

HRID 322348Notes

Reaction equation

HRID 322348 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].CS(O[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[N:25]=[C:26](/[CH:29]=[CH:30]/[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:27][CH:28]=2)=[CH:18][CH:17]=1)(=O)=O>CN(C)C=O.O>[N:1]1([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[N:25]=[C:26](/[CH:29]=[CH:30]/[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[O:27][CH:28]=3)=[CH:20][CH:21]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 155216743-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate

Product 1

HCID 155216754-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazoleYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazole (70 mg) in N,N-dimethylformamide (5 ml) was added, at 0° C., sodium hydride (60%, in oil, 50 mg). The mixture was stirred for one hour. To the reaction mixture was added 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate (350 mg). The mixture was stirred for 1.5 hour at 70° C. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The resulting crystalline product was recrystallized from ethyl acetate-hexane to give 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole (200 mg, 61%) as colorless prisms, mp 127-128° C.

Workup

  1. stirringThe mixture was stirred for 1.5 hour at 70° C
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting crystalline product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-91375f47bd06435ab199eec16fe1d933
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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