Triethylamine → 3-(4-Tert-butylphenyl)-5,5-dimethyl-imidazolidine-2,4-dione

HRID 546554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546554
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.C[O:23][C:24](=O)[C:25]([CH3:28])([CH3:27])[NH2:26]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:24](=[O:23])[C:25]([CH3:28])([CH3:27])[NH:26][C:12]2=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Produkt 1

HCID 576259723-(4-Tert-butylphenyl)-5,5-dimethyl-imidazolidine-2,4-dioneAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 15 g of 4-tert-butylphenyl-isocyanate in 200 mL of toluene are successively added 31.52 mL of triethylamine and 13.15 g of 2,2-dimethylglycine methyl ester hydrochloride. The reaction mixture is refluxed for 24 h, cooled to room temperature, poured into distilled water and extracted with ethyl acetate. The organic phase is washed successively with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is taken up in diethyl ether and the solid formed is filtered off and dried to give 17.75 g of 3-(4-tert-butylphenyl)-5,5-dimethyl-imidazolidine-2,4-dione, the characteristics of which are as follows:

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 24 h
  2. additionpoured
  3. distillationinto distilled water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed successively with water and with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customthe solid formed
  10. filtrationis filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d90c02ee6adf431e9a8831060f8eba9f
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935819B2

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