Sodium hydride → HCID 19966411, compound

HRID 260266Notes

Reaction equation

HRID 260266 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][CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O>CN(C)C=O>[C:1]1([C:7]2[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 695912-PhenylimidazoleHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 19966411HCID 19966411, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4.32 g of 2-phenyl-imidazole in solution in 25 ml of dimethylformamide were added over 75 minutes at ambient temperature to 1.73 g of sodium hydride in 5 ml of dimethylformamide and then, 10.97 g of N-(4-bromobutyl)-phthalimide in 33 ml of dimethylformamide were added. The mixture was stirred for 48 hours at ambient temperature and extraction was carried out with ethyl acetate, followed by drying. The solvent has evaporated and the residue was chromatographed on silica (eluant: ethyl acetate-methylethylamine 95-5). The residue was taken up in ether, chilled and the crystals were separated out and dried to obtain 1.11 g of the expected product melting at 82°-84° C.

Workup

  1. extractionextraction
  2. customby drying
  3. customThe solvent has evaporated
  4. customthe residue was chromatographed on silica (eluant: ethyl acetate-methylethylamine 95-5)
  5. temperaturechilled
  6. customthe crystals were separated out and
  7. customdried

Sources & evidence

ORD record
ord-3cabe975ce99435c90346efde21c7453
Source dataset
uspto-grants-1996_06
Patent number
US05527780

Reaction notes

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