Water → 1-(2-Phthalimidoethyl)-4,5-diphenylimidazole

HRID 362895Notes

Reaction equation

HRID 362895 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Cl[CH2:14][CH2:15][N:16]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:18]=[CH:17]1.O>CN(C=O)C.C(Cl)(Cl)Cl>[C:1]1(=[O:11])[N:5]([CH2:14][CH2:15][N:16]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:18]=[CH:17]2)[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

6

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 542225981-(2-Chloroethyl)-4,5-diphenylimidazole

Product 1

HCID 539687861-(2-Phthalimidoethyl)-4,5-diphenylimidazoleYield 73%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Step 2): A mixture of potassium phthalimide (0.21 g, 1.1 mmol) and 1-(2-chloroethyl)-4,5-diphenylimidazole (0.32 g, 1.1 mmol) in dry DMF (10 ml) was heated at 60°-70° C. for 6 hours. The reaction mixture was cooled, diluted with chloroform, poured into water and extracted with chloroform. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (40% ethyl acetate in chloroform) to give 1-(2-phthalimidoethyl)-4,5-diphenylimidazole (73.0%).

Workup

  1. temperaturewas heated at 60°-70° C. for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (40% ethyl acetate in chloroform)

Sources & evidence

ORD record
ord-b9b7c5b046e0459fb54543dbd79ec6ea
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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