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

HRID 1078407Notes

Reaction equation

HRID 1078407 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]>CN(C=O)C>[N:1]1([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
95 °C

Procedure

A solution of imidazole (13.6 g) in dry DMF (50 ml) was added dropwise to a stirred suspension of sodium hydride (8.0 g, 60% dispersion in oil) in dry DMF (250 ml) at ambient temperature under nitrogen for 2.5 hours. A slurry of N-(4-bromobutyl)phthalimide (53.6 g) in dry DMF (80 ml) was added and the mixture heated at 95° C. for 16 hours. The solvent was evaporated off under vacuum 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-[4-(imidazol-1-yl)butyl]phthalimide, m.p. 76°-79° C.

Workup

  1. customThe solvent was evaporated off under vacuum
  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-b25406fb1d44487fa9a75fb9c11408e2
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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