1,3-Dibromo-5,5-dimethylhydantoin → 2,4-Imidazolidinedione, 3-(4-amino-3-(trifluoromethyl)phenyl)-5,5-dimethyl-

HRID 1872322Notes

Reaction equation

HRID 1872322 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[C:4]([NH2:11])=[CH:3][CH:2]=1.Br[N:13]1[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15](Br)[C:14]1=[O:22].CC1(C)NC(=O)NC1=O>[Cu]=O.CC(N(C)C)=O>[NH2:11][C:4]1[CH:3]=[CH:2][C:1]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]2=[O:22])=[CH:6][C:5]=1[C:7]([F:9])([F:10])[F:8]

Participants

6

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 6491DimethylhydantoinHCID 69222-(Trifluoromethyl)aniline

Product 1

HCID 158384422,4-Imidazolidinedione, 3-(4-amino-3-(trifluoromethyl)phenyl)-5,5-dimethyl-Yield 174.6%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 31374DimethylacetamideSolvent2×

Procedure

100 g of O-trifluoromethylaniline is introduced at 20°±2° C. then 100 ml of dimethylacetamide is added while maintaining the same temperature. After cooling down under agitation at 0° C.±2° C. a solution of 88.8 g of dibromodimethylhydantoin and 100 ml of dimethylacetamide is then added over about 30 minutes while maintaining the temperature at 0° C.±2° C. The reaction medium is maintained under agitation for 30 minutes, then taken to 20° C.±2° C. and 40 g of dimethylhydantoin then 50 g copper oxide are added. The whole is heated under reflux for approximately 18 hours then cooled down to 20° C.±2° C., agitation is carried out for 30 minutes followed by filtering, separating and washing with 4×25 ml of dimethylacetamide. The resultant product is then poured into 300 ml of pure 22°Be ammonium hydroxide and 300 ml of demineralized water under agitation over 1 hour at 20° C.±2° C., agitation is continued for 1 hour at 20° C.±2° C. then the whole is cooled down to 0° C.±5° C. and is maintained under agitation for another hour, followed by separating, washing at 20° C.±2° C., with 100 ml of pure 22°Be ammonium hydroxide then with 4×100 ml of demineralized water and drying. In this way 155.8 g of expected product is obtained.

Workup

  1. temperaturewhile maintaining the same temperature
  2. additionis then added over about 30 minutes
  3. temperaturewhile maintaining the temperature at 0° C.±2° C
  4. temperatureThe reaction medium is maintained under agitation for 30 minutes
  5. customtaken to 20° C.±2° C.
  6. temperatureThe whole is heated
  7. temperatureunder reflux for approximately 18 hours
  8. temperaturethen cooled down to 20° C.±2° C.
  9. filtrationby filtering
  10. customseparating
  11. washwashing with 4×25 ml of dimethylacetamide
  12. additionThe resultant product is then poured into 300 ml of pure 22°Be ammonium hydroxide and 300 ml of demineralized water under agitation over 1 hour at 20° C.±2° C.
  13. waitagitation is continued for 1 hour at 20° C.±2° C.
  14. temperaturethe whole is cooled down to 0° C.±5° C.
  15. temperatureis maintained under agitation for another hour
  16. customby separating
  17. washwashing at 20° C.±2° C., with 100 ml of pure 22°Be ammonium hydroxide
  18. dry with materialwith 4×100 ml of demineralized water and drying

Sources & evidence

ORD record
ord-d8697db8eb7a4bf3b14fb3a88a87fbe2
Source dataset
uspto-grants-2000_08
Patent number
US06107488

Reaction notes

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