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Methane → 5,5-Dimethyl-3-{4-[(trifluoromethyl)sulfanyl]phenyl}imidazolidine-2,4-dione

HRID 546578
Notes
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Reaction equation

HRID 546578 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.[CH4:9].[F:10][C:11]([F:21])([F:20])[S:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.Cl.C([O:25]C(=O)CN(C)C)C.[CH2:32]([N:34]([CH2:37]C)CC)[CH3:33]>C1(C)C=CC=CC=1>[CH3:9][C:32]1([CH3:33])[NH:34][C:37](=[O:25])[N:17]([C:16]2[CH:18]=[CH:19][C:13]([S:12][C:11]([F:20])([F:10])[F:21])=[CH:14][CH:15]=2)[C:5]1=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 297MethaneHCID 8471TriethylamineHCID 10426DiphosgeneHCID 1230544-((Trifluoromethyl)thio)anilineHCID 86629091HCID 86629091, compound

Product 1

HCID 132680685,5-Dimethyl-3-{4-[(trifluoromethyl)sulfanyl]phenyl}imidazolidine-2,4-dione

Reagents, catalysts & solvents

1
HCID 1140TolueneSolvent3×

Conditions

Temperature
-20 °C

Procedure

To a solution of 8.5 mL of trichloromethyl chloroformate (diphosgene) in 250 mL of toluene are added 1.8 g of 3S charcoal. To this suspension cooled to −20° C. are added 10 g of 4-trifluoromethylthioaniline dissolved in 160 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 9.4 g of dimethylglycine ethyl ester hydrochloride in 90 mL of toluene is added, followed by 38 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 200 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 12 g of 5,5-dimethyl-3-{4-[(trifluoromethyl)thio]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-d829b3f9db12406881e8a7b79c947fca
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935819B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes