HCID 19875235, compound → HCID 19875200, compound

HRID 465693Notes

Reaction equation

HRID 465693 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]#[N:14])=[C:11]([C:15]#[N:16])[N:10](CC3C=CC=CC=3)[C:9]2=[O:24])=[CH:4][CH:3]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]#[N:14])=[C:11]([C:15]#[N:16])[NH:10][C:9]2=[O:24])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 19875235HCID 19875235, compound3×

Product 1

HCID 19875200HCID 19875200, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The product of Example 48, 1-(4-chlorophenyl)-4,5-dicyano-3-benzyl-1,3-dihydro-2H-imidazol-2-one, (XIII) (1.2 g, 3.6 mmol) was stirred in 50 mL of benzene. To this solution was added AlCl13 (1.9 g, 14.4 mmol) and the mixture was heated to reflux for one-half hour. The mixture was then poured onto water and extracted with ethyl acetate, then dried, filtered and evaporated via standard techniques. The residue was recrystallized from ethyl acetate/heptane to give 0.72 g of 1-(4-chlorophenyl)-4,5-dicyano-1,3-dihydro-2H-imidazol-2-one (XIV) (m.p. 242°-5° C.).

Workup

  1. additionTo this solution was added AlCl13 (1.9 g, 14.4 mmol)
  2. temperaturethe mixture was heated
  3. temperatureto reflux for one-half hour
  4. additionThe mixture was then poured onto water
  5. extractionextracted with ethyl acetate
  6. customdried
  7. filtrationfiltered
  8. customevaporated via standard techniques
  9. customThe residue was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-8c06a99fbdf44e068db07d3d48294344
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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