Methane → 5,5-Dimethyl-3-[3-nitro-4-(trifluoromethoxy)phenyl]imidazolidine-2,4-dione

HRID 546573Notes

Reaction equation

HRID 546573 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.[CH4:9].[N+:10]([C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][C:21]([F:24])([F:23])[F:22])[NH2:16])([O-:12])=[O:11].Cl.C([O:28]C(=O)CN(C)C)C.[CH2:35]([N:37]([CH2:40]C)CC)[CH3:36]>C1(C)C=CC=CC=1>[CH3:9][C:35]1([CH3:36])[NH:37][C:40](=[O:28])[N:16]([C:15]2[CH:17]=[CH:18][C:19]([O:20][C:21]([F:22])([F:23])[F:24])=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[C:5]1=[O:4]

Participants

7

Reactant 5

HCID 297MethaneHCID 8471TriethylamineHCID 10426DiphosgeneHCID 6136943-Nitro-4-(trifluoromethoxy)anilineHCID 86629091HCID 86629091, compound

Product 1

HCID 576259905,5-Dimethyl-3-[3-nitro-4-(trifluoromethoxy)phenyl]imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
-20 °C

Procedure

To a solution of 15 mL of trichloromethyl chloroformate (diphosgene) in 500 mL of toluene are added 3 g of 3S charcoal. To this suspension cooled to −20° C. are added 20 g of 3-nitro-4-trifluoromethoxyaniline dissolved in 400 mL of toluene. The reaction mixture is gradually warmed to room temperature and then refluxed for 4 hours. After cooling to room temperature, a suspension of 18 g of dimethylglycine ethyl ester hydrochloride in 150 mL of toluene is added, followed by 66 mL of triethylamine, and the reaction mixture is refluxed for 15 hours. After filtering through Celite, the filtrate is concentrated under reduced pressure and the residue is taken up in 500 mL of dichloromethane, washed with three times 100 mL of water, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is then triturated in diethyl ether and the solid formed is filtered off and dried to give 7.8 g of 5,5-dimethyl-3-[3-nitro-4-(trifluoromethoxy)phenyl]imidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction mixture is gradually warmed to room temperature
  2. temperaturerefluxed for 4 hours
  3. temperatureAfter cooling to room temperature
  4. additionis added
  5. temperaturethe reaction mixture is refluxed for 15 hours
  6. filtrationAfter filtering through Celite
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. washwashed with three times 100 mL of water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is then triturated in diethyl ether
  13. customthe solid formed
  14. filtrationis filtered off
  15. customdried

Sources & evidence

ORD record
ord-ee501e57d6a6445497e40404afe975f4
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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