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

HRID 1154332Notes

Reaction equation

HRID 1154332 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Na].Br[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22]>CN(C)C=O>[N:1]1([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3[C:14](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]2=[O:22])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 93575N-(4-Bromobutyl)phthalimideHCID 57373095Imidazole sodium

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.3 g. of sodium imidazole, 100 ml. of dimethylformamide and 19.7 g. of N-(4-bromobutyl)-phthalimide was heated on a steam bath for 6 hours and then concentrated to remove volatile material. The residue was boiled with 150 ml. of toluene and the toluene layer was decanted and concentrated. The residue was triturated with diethyl ether and cooled, giving N-[4-(1H-imidazol-1-yl)butyl]-isoindole-1,3(2H)-dione (m.p. 75°-77° C.) which was recovered by filtration.

Workup

  1. additionA mixture of 6.3 g
  2. concentrationconcentrated
  3. customto remove volatile material
  4. customof toluene and the toluene layer was decanted
  5. concentrationconcentrated
  6. customThe residue was triturated with diethyl ether
  7. temperaturecooled

Sources & evidence

ORD record
ord-e25bd4bf1f5742f797b06a9ce33624d1
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

Loading…