Imidazole → HCID 9861000, compound

HRID 2393501Notes

Reaction equation

HRID 2393501 reaction equation
Cl[CH:2]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)[CH3:3].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[CH:5]1[C:6]2[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[CH:16][C:4]=1[CH:2]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[CH3:3]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 145724842-(1-Chloroethyl)-9H-fluorene

Product 1

HCID 9861000HCID 9861000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The thus obtained 2-(1-chloroethyl)-9H-fluorene was dissolved in 20 ml of N,N-dimethylformamide, and the solution was mixed with imidazole (2.72 g), followed by stirring at 100° C. for 2 hours. The solvent was evaporated under a reduced pressure, and water was added to the resulting residue, followed by extraction with chloroform. The chloroform layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure and then the resulting residue was purified by silica gel column chromatography to obtain crude crystals from the eluate of a mixed solvent of chloroform and methanol (200:1). By recrystallizing the crude crystals from a mixed solvent of ethyl acetate and ether, 0.6 g of 1-[1-(9H-fluoren-2-yl) ethyl]-1H-imidazole was obtained.

Workup

  1. customThe solvent was evaporated under a reduced pressure, and water
  2. additionwas added to the resulting residue
  3. extractionfollowed by extraction with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography
  8. customto obtain crude crystals from the eluate of a mixed solvent of chloroform and methanol (200:1)
  9. customBy recrystallizing the crude crystals from a mixed solvent of ethyl acetate and ether

Sources & evidence

ORD record
ord-e6d696d5ed244227995ef5eabef22e6c
Source dataset
uspto-grants-1998_09
Patent number
US05807880

Reaction notes

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