Imidazole → N-[4-(imidazol-1-yl)butyl]phthalimide

HRID 1589193Notes

Reaction equation

HRID 1589193 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>[Ag].CN(C)C=O>[N:17]1([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 13290795N-[4-(imidazol-1-yl)butyl]phthalimide

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.1 mole of 2-(4-bromobutyl)-1H-isoindole-1,3(2H)-dione and 0.1 mole of the silver salt of imidazole were heated in 300 ml. of dimethylformamide for 8 hours. The reaction mixture was concentrated to remove the solvent and the residue was boiled with 200 ml. of toluene and filtered to remove the insoluble material. The toluene layer was concentrated and the desired product was purified by HPLC using ethyl acetate and a silica gel column.

Workup

  1. temperaturewere heated in 300 ml
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the solvent
  4. filtrationof toluene and filtered
  5. customto remove the insoluble material
  6. concentrationThe toluene layer was concentrated
  7. customthe desired product was purified by HPLC

Sources & evidence

ORD record
ord-df32eb2b371541369532891b60c44b3e
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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