Imidazole → HCID 20251865, compound

HRID 1284487Notes

Reaction equation

HRID 1284487 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][CH2:11][C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]2[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=2[N:13]=1.O.O.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>CN(C)C=O.O.C(OCC)C.C(O)C>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[N:1]1([CH2:9][CH2:10][CH2:11][C:12]2[N:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:15]3[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

9

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 20251885HCID 20251885, compound

Product 1

HCID 20251865HCID 20251865, compoundYield 92.1%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazole (226 mg) in N,N-dimethylformamide (9 ml) was added sodium hydride (60% in oil, 140 mg) with stirring and ice-cooling. The mixture was stirred for 15 minutes at the same temperature and for 1 hour at 100° C. To the resultant mixture, after cooling, was added 2-(3-chloropropyl)-1-phenyl-1H-benzimidazole (0.9 g) and the mixture was stirred for 1 hour at 100° C. After being cooled, the reaction mixture was diluted with water and extracted with dichloromethane. The combined extract was washed with water and saturated aqueous sodium chloride in turn, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give an oily residue, which was subjected to column chromatography on silica gel (9 g) eluting with a mixture of dichloromethane and methanol (50:1) to give an oil. To a solution of the oil in diethyl ether (30 ml) was added a solution of oxalic acid dihydrate (321 mg) in ethanol to give an oily precipitate. The oily precipitate was triturated in ethanol to give powder of 2-[3-(imidazol-1-yl)propyl]-1-phenyl-1H-benzimidazole oxalate (920 mg).

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred for 15 minutes at the same temperature and for 1 hour at 100° C
  3. stirringthe mixture was stirred for 1 hour at 100° C
  4. temperatureAfter being cooled
  5. extractionextracted with dichloromethane
  6. extractionThe combined extract
  7. washwas washed with water and saturated aqueous sodium chloride in turn
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customto give an oily residue, which
  11. washeluting with a mixture of dichloromethane and methanol (50:1)
  12. customto give an oil
  13. customto give an oily precipitate
  14. customThe oily precipitate was triturated in ethanol

Sources & evidence

ORD record
ord-5fa1becfec08437a97bffb14efc47143
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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