1,3-Dibromo-5,5-dimethylhydantoin → 4-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile

HRID 1872326Notes

Reaction equation

HRID 1872326 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1N.C[C:13]([N:15](C)C)=O.Br[N:19]1[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[N:21](Br)[C:20]1=[O:28].C(OC(C)C)(C)C>O>[CH3:25][C:22]1([CH3:26])[C:23](=[O:24])[N:19]([C:8]2[CH:7]=[CH:6][C:4]([C:13]#[N:15])=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:9]=2)[C:20](=[O:28])[NH:21]1

Participants

6

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 69222-(Trifluoromethyl)anilineHCID 7914Diisopropyl EtherHCID 31374Dimethylacetamide

Product 1

HCID 111622854-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 g of ortho trifluoromethylaniline and 200 ml of dimethylacetamide are introduced and the reaction medium is cooled down to 0°±2° C. 88.8 g of dibromo-dimethyl hydantoin is added over 30 minutes at 0°±2° C., the temperature is maintained at 0°±2° C. and agitation is carried out at 0°±2° C . for 15 minutes. Then the temperature is allowed to rise to 20° C. and the whole is poured into 200 ml of demineralized water at 20°±2° C. Agitation is carried out for 15 minutes, 400 ml of isopropyl ether is added, the aqueous phase is decanted and the organic phase is washed with 2×100 ml of demineralized water, the aqueous phases are reextracted with 100 ml of isopropyl ether and the combined organic phases are dried, filtered and washed with 2×20 ml of isopropyl ether. Concentration is carried out a temperature of 30-40° C. and in this way 149 g of expected product (orangy-brown oil) is obtained.

Workup

  1. temperaturethe reaction medium is cooled down to 0°±2° C
  2. temperaturethe temperature is maintained at 0°±2° C.
  3. customis carried out at 0°±2° C
  4. customto rise to 20° C.
  5. waitAgitation is carried out for 15 minutes
  6. customthe aqueous phase is decanted
  7. washthe organic phase is washed with 2×100 ml of demineralized water
  8. customthe combined organic phases are dried
  9. filtrationfiltered
  10. washwashed with 2×20 ml of isopropyl ether
  11. concentrationConcentration
  12. customa temperature of 30-40° C.

Sources & evidence

ORD record
ord-ef63c6ecf7aa4751a1faf19a0481b173
Source dataset
uspto-grants-2000_08
Patent number
US06107488

Reaction notes

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