N-3-Bromopropylphthalimide → N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide

HRID 1078408Notes

Reaction equation

HRID 1078408 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>CN(C=O)C>[C:1]1([C:7]2[N:11]([CH2:15][CH2:16][CH2:17][N:18]3[C:22](=[O:23])[C:21]4=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]4[C:19]3=[O:28])[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 695912-Phenylimidazole

Product 1

HCID 19429428N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
100 °C

Procedure

A solution of 2-phenylimidazole (14.4 g) in dry DMF (25 ml) was added dropwise to a stirred suspension of sodium hydride (4.0 g, 60% dispersion in oil) in dry DMF (125 ml) at ambient temperature under nitrogen for 2 hours. A slurry of N-(3-bromopropyl)phthalimide (25.5 g) in dry DMF (40 ml) was added and the mixture heated at 100° C. for 16 hours. The solvent was evaporated off and the residue was extracted with hot toluene. The combined toluene extracts were evaporated to dryness and the residue triturated with ether and dried to give N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide, m.p. 109°-110.5° C.

Workup

  1. customThe solvent was evaporated off
  2. extractionthe residue was extracted with hot toluene
  3. customThe combined toluene extracts were evaporated to dryness
  4. customthe residue triturated with ether
  5. customdried

Sources & evidence

ORD record
ord-c5807d56ecbd45a1af0a492341dacea5
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

Loading…