Imidazole → HCID 20377655, compound

HRID 2052308Notes

Reaction equation

HRID 2052308 reaction equation
Cl[C:2]1([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9](=[O:16])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>C(#N)C>[N:24]1([C:2]2([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9](=[O:16])[C:8]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 20377648HCID 20377648, compound

Product 1

HCID 20377655HCID 20377655, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

36.2 g (0.113 mol) of 9-chloro-9,10-dihydro-9-(4-methylphenyl)-10-oxo-anthracene and 20.4 g (0.3 mol) of imidazole in 400 ml of absolute acetonitrile are heated under reflux for 5 hours. Thereafter, the solvent is distilled off in vacuo and the residue is taken up in 500 ml of methylene chloride. The methylene chloride solution is washed twice with 1,000 ml of water each time and the organic phase is separated off, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The yellow, oily residue is recrystallised from 300 ml of acetonitrile. 16.5 g (40.6% of theory) of 9,10-dihydro-9-imidazol-1-yl-9-(4-methylphenyl)-10-oxo-anthracene of melting point 200°-204° C. are obtained.

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationThereafter, the solvent is distilled off in vacuo
  3. washThe methylene chloride solution is washed twice with 1,000 ml of water each time
  4. customthe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent in vacuo
  8. customThe yellow, oily residue is recrystallised from 300 ml of acetonitrile

Sources & evidence

ORD record
ord-2ae2c7bf839a4289a2e0e664e4025202
Source dataset
uspto-grants-1980_01
Patent number
US04183940

Reaction notes

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