Pyridine → 3-Benzyl-2,5-dioxoimidazolidine 1-hexylcarboxamide

HRID 1028151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028151
[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(CCCCCC)=C=[O:17].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:2]([C:1]([NH2:8])=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 75659Hexyl isocyanate2×HCID 27354851-Benzylimidazolidine-2,4-dione

Produkt 1

HCID 1317314083-Benzyl-2,5-dioxoimidazolidine 1-hexylcarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

1-Benzylimidazolidine-2,4-dione (100 mg, 0.526 mmol) and 1-isocyanatohexane (80.3 mg, 0.63 mmol) and, if required, a catalytic amount of 4-dimethylaminopyridine were dissolved in 10 ml of toluene and 0.5 ml of pyridine and stirred at 115° C. for 6 h. Then a further 80 mg of 1-isocyanatohexane were added, and the mixture was stirred at 115° C. for a further 6 h. The reaction mixture was concentrated and the residue was taken up in ethyl acetate and H2O, and the org. phases were washed twice with water, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 11.3 mg (7%), M+H+:318.14.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. washphases were washed twice with water
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-fe93801de6af459f8d4d780a3c9f400a
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735437B2

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