Potassium Cyanide → 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one

HRID 465689Notes

Reaction equation

HRID 465689 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:16](Cl)=[C:15]([C:18]#[N:19])[N:14]([CH2:20]CC)[C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1.[C-]#N.[K+].[C:28]([Cu])#[N:29]>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:16]([C:28]#[N:29])=[C:15]([C:18]#[N:19])[N:14]([CH3:20])[C:13]2=[O:23])=[C:4]([F:24])[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-one2×HCID 178418546HCID 178418546, compound

Product 1

HCID 198752171-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 3, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-5-chloro-4-cyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (V) (0.14 9, 0.4 mmol) was stirred in 20 mL dimethylformamide. To this mixture was added KCN (0.13 g, 2.0 mmol) and the resulting mixture was heated to reflux for ten minutes, however some starting material remained. The mixture was again heated to reflux one hour with the addition of CuCN (0.18 g, 2.0 mmol). The mixture was cooled, poured onto water, and extracted three times with 50 mL ethyl acetate. The organic solution was dried over MgSO4, filtered, and evaporated, then chromatographed to give approximately 30 mg of a glassy oil. Recrystallization with ethyl ether/hexane gave 22 mg of 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (VI) (m.p. 124°-6° C.).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for ten minutes
  3. temperatureThe mixture was again heated
  4. temperatureThe mixture was cooled
  5. additionpoured onto water
  6. extractionextracted three times with 50 mL ethyl acetate
  7. dry with materialThe organic solution was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customchromatographed

Sources & evidence

ORD record
ord-46669dfce97e4175964cf4c99511e93a
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

Loading…