3-[4-Iodo-3-(trifluoromethyl)phenyl]-5,5-dimethyl-2,4-imidazolidinedione → 4-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile

HRID 1872324Notes

Reaction equation

HRID 1872324 reaction equation
[CH3:1][C:2]1([CH3:20])[NH:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11](I)=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=2)[C:3]1=[O:19].[Cu](C#N)[C:22]#[N:23]>CN(C)C=O>[CH3:1][C:2]1([CH3:20])[C:3](=[O:19])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:22]#[N:23])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=2)[C:5](=[O:7])[NH:6]1

Participants

4

Reactant 2

HCID 158384433-[4-Iodo-3-(trifluoromethyl)phenyl]-5,5-dimethyl-2,4-imidazolidinedioneHCID 178418260HCID 178418260, compound

Product 1

HCID 111622854-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrileYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

184 g of the product of Example 2 is introduced at 20°±2° C. and 66.15 g of copper cyanide and 420 ml of dimethylformamide are added under agitation the whole is heated while distilling the methylene chloride until a temperature of 130° C. is obtained in the reaction medium and then it is maintained for 5 hours under agitation at this temperature. The medium is cooled down to 20°±2° C. under agitation, maintained for 1 hour under these conditions followed by separation and washing with 3×0.3 vol of dimethylformamide. Then 700 ml of pure 22°Be ammonium hydroxide and 700 ml of demineralized water are added to the mixture agitated at 20°±2° C. Agitation is carried out for 1 hour at 20°±2° C. then the whole is cooled down to 0°±5° C., maintained for 1 hour under agitation at 0°±5° C., followed by separating and washing with 2×140 ml of pure 22°Be ammonium hydroxide at 20°±2° C. then with 4×140 ml of demineralized water then drying. Purification is carried out by adding 1105 ml of ethyl acetate then taking to reflux under agitation and then 12.3 g of acticarbon black CX is added. The reaction medium is maintained under agitation under reflux for 30 minutes, then filtered, followed by washing with 3×61 ml of boiling ethyl acetate, concentration under agitation, cooling down under agitation to 0°±2° C. and maintaining under these conditions for 2 hours. Separation, washing with 3×37 ml of ethyl acetate at 0°±2° C. and drying are carried out. In this way 103.7 g of expected product (clear beige powder) is obtained.

Workup

  1. temperatureis heated
  2. distillationwhile distilling the methylene chloride until a temperature of 130° C.
  3. customis obtained in the reaction medium
  4. temperatureit is maintained for 5 hours under agitation at this temperature
  5. temperatureThe medium is cooled down to 20°±2° C. under agitation
  6. temperaturemaintained for 1 hour under these conditions
  7. customfollowed by separation
  8. washwashing with 3×0.3 vol of dimethylformamide
  9. additionThen 700 ml of pure 22°Be ammonium hydroxide and 700 ml of demineralized water are added to the mixture
  10. temperaturethe whole is cooled down to 0°±5° C.
  11. temperaturemaintained for 1 hour under agitation at 0°±5° C.
  12. customby separating
  13. washwashing with 2×140 ml of pure 22°Be ammonium hydroxide at 20°±2° C.
  14. dry with materialwith 4×140 ml of demineralized water then drying
  15. customPurification
  16. additionby adding 1105 ml of ethyl acetate
  17. temperatureto reflux under agitation
  18. addition12.3 g of acticarbon black CX is added
  19. temperatureThe reaction medium is maintained under agitation
  20. temperatureunder reflux for 30 minutes
  21. filtrationfiltered
  22. washby washing with 3×61 ml of boiling ethyl acetate, concentration under agitation
  23. temperaturecooling down under agitation to 0°±2° C.
  24. temperaturemaintaining under these conditions for 2 hours
  25. customSeparation
  26. washwashing with 3×37 ml of ethyl acetate at 0°±2° C.
  27. customdrying

Sources & evidence

ORD record
ord-63690e9cfcce4572b486e25a0b610369
Source dataset
uspto-grants-2000_08
Patent number
US06107488

Reaction notes

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