Water → HCID 19875262, compound

HRID 465697Notes

Reaction equation

HRID 465697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](Br)=[C:11]([C:14]#[N:15])[N:10]([CH3:16])[C:9]2=[O:17])=[CH:4][CH:3]=1.[F-:18].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([F:18])=[C:11]([C:14]#[N:15])[N:10]([CH3:16])[C:9]2=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 19875267HCID 19875267, compound2×

Product 1

HCID 19875262HCID 19875262, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of the product of Example 66, 1-(4-chlorophenyl)-5-bromo-4-cyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (0.4 g, 1.3 mmol) and potassium fluoride (0.14 g, 2.66 mmol) in 100 mL of dry dimethyl sulfoxide was heated to 130° C. for two hours, then cooled and poured into 100 mL of water. The product was extracted into ethyl acetate, washed with saturated brine solution, dried, and concentrated to an oil. The oil was chromatographed through silica gel (25:75 ethyl acetate:petroleum ether). Collection of the appropriate fractions furnished 0.14 g of 1-(4-chlorophenyl)-4-cyano-5-fluoro-3-methyl-1,3-dihydro-2H-imidazol-2-one (m.p. 105° C.).

Workup

  1. temperaturecooled
  2. extractionThe product was extracted into ethyl acetate
  3. washwashed with saturated brine solution
  4. customdried
  5. concentrationconcentrated to an oil
  6. customThe oil was chromatographed through silica gel (25:75 ethyl acetate:petroleum ether)
  7. customCollection of the appropriate fractions

Sources & evidence

ORD record
ord-55898447420f4e7a8d485f7653c6c94d
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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