Imidazole → HCID 20377665, compound

HRID 2052312Notes

Reaction equation

HRID 2052312 reaction equation
Cl[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9](Cl)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>C(#N)C>[N:29]1([C:2]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]([N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 3007259,10-Dichloro-9,10-diphenyl-9,10-dihydroanthracene

Product 1

HCID 20377665HCID 20377665, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15 g (0.04 mol) of 9,10-dichloro-9,10-dihydro-9,10-diphenyl-anthracene and 17.7 g (0.24 mol) of imidazole in 250 ml of absolute acetonitrile are heated under reflux for 6 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 500 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 residue is heated in 300 ml of methanol and filtered. The filtrate is concentrated and the oil which remains is triturated with 50 ml of diisopropyl ether, whereupon it crystallises. 10 g (54% of theory) of 9,10-diimidazol-1-yl-9,10-dihydro-9,10-diphenyl-anthracene of melting point 258°-260° C. are obtained.

Workup

  1. temperatureunder reflux for 6 hours
  2. distillationThereafter, the solvent is distilled off in vacuo
  3. washThe methylene chloride solution is washed twice with 500 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. temperatureThe residue is heated in 300 ml of methanol
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated
  11. customthe oil which remains is triturated with 50 ml of diisopropyl ether, whereupon it
  12. customcrystallises

Sources & evidence

ORD record
ord-07daadda327b4dbdadfeca125018b649
Source dataset
uspto-grants-1980_01
Patent number
US04183940

Reaction notes

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