Iodoethane → HCID 67106543, compound

HRID 1910818Notes

Reaction equation

HRID 1910818 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:16](N(CC)C(C)C)(C)[CH3:17].C(I)C>CN(C=O)C>[CH2:16]([N:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][C:7]1[CH:14]=[CH:15][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 104428612-(4-NITRO-BENZYL)-1H-IMIDAZOLE

Product 1

HCID 67106543HCID 67106543, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-(4-nitro-benzyl)-1H-imidazole (1.58 g, 7.37 mmol) in DMF (10 mL) was added N,N-diisopropylethyl amine (1.93 mL, 11.05 mmol) and heated to 5° C. for 30 min. Ethyl iodide (1.18 mL, 7.37 mmol) was added dropwise and the reaction mixture heated to reflux for 6 h. The solvent was evaporated under reduced pressure, the residue dissolved in dichloromethane and washed with water. The organic layer was dried over sodium sulfate, filtered, evaporated and the residue purified by column chromatography over silica gel (60-120 mesh) using 3% methanol/chloroform as eluent to afford 1-ethyl-2-(4-nitrobenzyl)-1H-imidazole (0.35 g, 21%).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 6 h
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-84ed1f57970242a3b84ac3784f573e48
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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