Methane → Methyl 2-[4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)phenyl]-2-methylpropanoate

HRID 546633Notes

Reaction equation

HRID 546633 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.[CH4:9].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1.Cl.C[O:26][C:27](=O)[CH2:28][N:29](C)C.[C:33]1(C)C=CC=CC=1>C(OCC)C.C(N(CC)CC)C>[CH3:9][C:28]1([CH3:33])[C:27](=[O:26])[N:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=2)[C:5](=[O:4])[NH:29]1

Participants

8

Reactant 5

HCID 297MethaneHCID 1140Toluene2×HCID 10426DiphosgeneHCID 584407Methyl 2-(4-aminophenyl)-2-methylpropanoateHCID 12546525N,N-Dimethylglycine methyl ester HCl

Product 1

HCID 57626011Methyl 2-[4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)phenyl]-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 3.7 mL of trichloromethyl chloroformate (diphosgene) in 120 mL of toluene, under argon, is added 1 g of 3S charcoal. To this suspension cooled to −20° C. are added 4.3 g of methyl 2-(4-aminophenyl)-2-methylpropanoate obtained in stage b) below dissolved in 130 mL of toluene. The reaction mixture is gradually warmed to room temperature and then refluxed for 4 hours. After cooling to room temperature, 16.6 mL of triethylamine and 4.25 g of dimethylglycine methyl ester hydrochloride are added and the reaction mixture is refluxed for 24 hours and then concentrated under reduced pressure. The residue obtained is taken up in ethyl ether and water, the phases are separated and the organic phase is dried over magnesium sulphate, filtered and then concentrated under reduced pressure to give 1.23 g of methyl 2-[4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)phenyl]-2-methylpropanoate, 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. temperaturethe reaction mixture is refluxed for 24 hours
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwater, the phases are separated
  8. dry with materialthe organic phase is dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ab5f75d059d44a29af5c14dbae99ff5
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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