Aluminum(III) Chloride → 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one

HRID 465691Notes

Reaction equation

HRID 465691 reaction equation
[Cl:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([N:10]2[C:14]([C:15]#[N:16])=[C:13]([C:17]#[N:18])[N:12]([CH3:19])[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.ClC1C(OCC#C)=CC(N2C(C#N)=C(C#N)N(CCC)C2=O)=C(F)C=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:10]2[C:14]([C:15]#[N:16])=[C:13]([C:17]#[N:18])[N:12]([CH3:19])[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 198752051-(4-chloro-2-fluoro-5-methoxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-oneHCID 198752701-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 198751891-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The product of Example 29, 1-(4-chloro-2-fluoro-5-methoxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (VI) (2.7 g, 8.82 mmol) was stirred in 100 mL benzene. To this mixture was added AlCl3 (4.68 g, 35.3 mmol) and the mixture was heated to reflux for 15 minutes. The mixture was cooled to room temperature, poured onto water, and extracted three times with 100 mL ethyl acetate. The organic solution was washed with water and brine, dried over MgSO4, filtered, and evaporated. The crude product was purified by elution from a short silica gel column. Recrystallization with ethyl acetate/heptane gave 1.6 g of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (VIII) (m.p. 210°-12° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. additionpoured onto water
  4. extractionextracted three times with 100 mL ethyl acetate
  5. washThe organic solution was washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by elution from a short silica gel column
  10. customRecrystallization with ethyl acetate/heptane

Sources & evidence

ORD record
ord-614078ff6af04ddda90fab7e72837125
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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