Potassium Cyanide → 1-(4-chlorophenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

HRID 465687Notes

Reaction equation

HRID 465687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](Cl)=[C:11]([C:14]#[N:15])[N:10]([CH2:16][CH2:17][CH3:18])[C:9]2=[O:19])=[CH:4][CH:3]=1.ClC1C(OCC#C)=C[C:24]([N:31]2C(Cl)=C(C#N)N(CCC)C2=O)=C(F)C=1.[C-]#N.[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:24]#[N:31])=[C:11]([C:14]#[N:15])[N:10]([CH2:16][CH2:17][CH3:18])[C:9]2=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 198752291-(4-chloro-2-fluoro-5-propargyloxyphenyl)-5-chloro-4-cyano-3-propyl-1,3-dihydro-2 H-imidazol-2-oneHCID 198752461-(4-chlorophenyl)-5-chloro-4-cyano-3-propyl-1,3-dihydro-2H-imidazole-2-one

Product 1

HCID 198752211-(4-chlorophenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 1, 1-(4-chlorophenyl)-5-chloro-4-cyano-3-propyl-1,3-dihydro-2H-imidazol-2-one (V) (0.75 g, 2.5 mmol), was stirred in 25 mL of dimethylformamide. To this mixture was added KCN (0.5 g, 7.5 mmol) and the resulting mixture was heated to reflux for ten minutes, cooled, poured onto water, and extracted three times with 50 mL ethyl acetate. This material was then dried, filtered, and evaporated via standard techniques to give 0.38 g of 1-(4-chlorophenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one (VI) recrystallized from ethyl acetate/hexane (m.p. 163°-5° C.).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for ten minutes
  3. temperaturecooled
  4. additionpoured onto water
  5. extractionextracted three times with 50 mL ethyl acetate
  6. customThis material was then dried
  7. filtrationfiltered
  8. customevaporated via standard techniques

Sources & evidence

ORD record
ord-1af70db5c26e409c8f4bc3538f2bf59f
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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