Diethyl Ether → 4-[2-(4-Propylphenoxy)ethyl]-1H-imidazole

HRID 726259

Reaction equation

HRID 726259 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:4][CH3:5].Cl.Cl[CH2:15][CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1.C(OCC)C>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:15][CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 125804-PropylphenolHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 1784392714-[2-(4-Propylphenoxy)ethyl]-1H-imidazole

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

240 mg (60% in oil; 6 mmol) of sodium hydride are slowly added to a solution of 1.63 g (12 mmol) of 4-propylphenol in 10 ml of dimethylformamide and the mixture is stirred at room temperature for 1 hour. 200 mg (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide are added and the mixture is stirred at 80° C. for 3 days. The reaction mixture is cooled and 150 ml of diethyl ether are added. The precipitate is separated by filtration and the filtrate is evaporated under reduced pressure to give a residue which is purified by preparative high performance chromatography. The title compound is converted to the oxalate (from an ethanol/diethyl ether mixture), M.p.: 168°-171° C.

Workup

  1. stirringthe mixture is stirred at 80° C. for 3 days
  2. temperatureThe reaction mixture is cooled
  3. customThe precipitate is separated by filtration
  4. customthe filtrate is evaporated under reduced pressure
  5. customto give a residue which
  6. customis purified by preparative high performance chromatography

Sources & evidence

ORD record
ord-e2d344935a8e4b058f1d5b877e6be2c7
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Linked notes

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