Sodium hydride → HCID 178436664, compound

HRID 726264Notes

Reaction equation

HRID 726264 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:4].Cl.Cl[CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)=[CH:7][CH:6]=1)[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 312424-EthylphenolHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178436664HCID 178436664, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

180 mg (60% in oil; 4.5 mmol) of sodium hydride are slowly added to a solution of 1.1 g (9 mmol) of 4-ethylphenol in 7 ml of dimethylformamide and the mixture is stirred at room temperature for 2 hours. 150 mg (0.9 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalyst) are added and the mixture is stirred at 80° C. for 3 days. The solvent is concentrated and 50 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 subjected to column chromatography through silica gel (first eluent ethyl acetate, second eluent 95/5 ethyl acetate/methanol). The title compound is then purified by preparative chromatography and then converted to the oxalate which, after crystallization from an ethanol/diethyl ether mixture, melts at 178° C.

Workup

  1. stirringthe mixture is stirred at 80° C. for 3 days
  2. concentrationThe solvent is concentrated
  3. addition50 ml of diethyl ether are added
  4. customThe precipitate is separated by filtration
  5. customthe filtrate is evaporated under reduced pressure
  6. customto give a residue which
  7. customThe title compound is then purified by preparative chromatography
  8. customafter crystallization from an ethanol/diethyl ether mixture, melts at 178° C.

Sources & evidence

ORD record
ord-d67be9537b164d3cb89a60df3a32d026
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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