4-(4-Fluorobenzoyl)-5-methyl-1,3-dihydro-2H-imidazol-2-one → HCID 13815975, compound

HRID 637305Notes

Reaction equation

HRID 637305 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[NH:9][C:10](=[O:14])[NH:11][C:12]=2[CH3:13])=[O:7])=[CH:4][CH:3]=1.[CH3:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1>O>[CH3:13][C:12]1[NH:11][C:10](=[O:14])[NH:9][C:8]=1[C:6](=[O:7])[C:5]1[CH:15]=[CH:16][C:2]([N:21]2[CH:22]=[C:18]([CH3:17])[N:19]=[CH:20]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 155675394-(4-Fluorobenzoyl)-5-methyl-1,3-dihydro-2H-imidazol-2-oneHCID 178418800HCID 178418800, compound

Product 1

HCID 13815975HCID 13815975, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

4-(4-Fluorobenzoyl)-1,3-dihydro-5-methyl-2H-imidazol-2-one (6.6 g, 30 mmol) is combined with 4-methyl-1H-imidazole (33 g, ca. 400 mmol) in a sealed flask and the mixture heated with stirring at ca. 140° C. overnight. The mixture is cooled, water (120 mL) added and the mixture stirred in an ice bath. The suspension is filtered and the filter cake washed with water and acetone. The solid is heated under reflux in a mixture of 2-propanol (300 mL) and water (200 mL) until dissolution is complete. The solution is filtered, reheated to dissolve some precipitated solid and allowed to cool slowly to room temperature. After 2.5 days the mixture is cooled in ice for 2 hr, the solid collected by filtration, washed with acetone, and dried in vacuo at 105° C. for 23 hr to produce the title compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureThe mixture is cooled
  3. stirringthe mixture stirred in an ice bath
  4. filtrationThe suspension is filtered
  5. washthe filter cake washed with water and acetone
  6. temperatureThe solid is heated
  7. temperatureunder reflux in a mixture of 2-propanol (300 mL) and water (200 mL) until dissolution
  8. filtrationThe solution is filtered
  9. dissolutionto dissolve some precipitated solid
  10. temperatureto cool slowly to room temperature
  11. temperatureAfter 2.5 days the mixture is cooled in ice for 2 hr
  12. filtrationthe solid collected by filtration
  13. washwashed with acetone
  14. customdried in vacuo at 105° C. for 23 hr

Sources & evidence

ORD record
ord-8861fb08a71c41c491dbdaf12cd014b4
Source dataset
uspto-grants-1985_12
Patent number
US04556665

Reaction notes

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