Imidazole → 3-Chloro-1-imidazol-1-yl-4-phenylisoquinoline

HRID 1657581Notes

Reaction equation

HRID 1657581 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([Cl:25])[N:10]=1>COCCOC>[Cl:25][C:11]1[N:10]=[C:9]([N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)[C:18]2[C:13]([C:12]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 21534896HCID 21534896, compound

Product 1

HCID 1939953-Chloro-1-imidazol-1-yl-4-phenylisoquinoline

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

15 g (0.5 mole) of an 80% suspension of sodium hydride in mineral oil were introduced, while stirring, into a solution of 37.5 g (0.6 mole) of imidazole in 250 ml of absolute 1,2-dimethyoxyethane. The whole was heated for 30 minutes to the boil and then a solution of 109.6 g (0.4 mole) of 1,3-dichloro-4-phenylisoquinoline in 100 ml of absolute 1,2-dimethoxyethane was added dropwise. The mixture was then boiled for 3 hours under reflux, the solvent was distilled off under reduced pressure and the residue was dissolved in a mixture of methylene chloride and water. The organic phase was washed with water, the sol-was removed under reduced pressure and the product was recrystallized from toluene. M.p. 165° to 168°.

Workup

  1. temperatureThe whole was heated for 30 minutes to the boil
  2. temperatureunder reflux
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in a mixture of methylene chloride and water
  5. washThe organic phase was washed with water
  6. customthe sol-was removed under reduced pressure
  7. customthe product was recrystallized from toluene

Sources & evidence

ORD record
ord-28feb70e598841419f02ba4b9c1caa7f
Source dataset
uspto-grants-1976_06
Patent number
US03961062

Reaction notes

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