1-Adamantanecarbonyl chloride → 5-carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate

HRID 443584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443584
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:14]([C:17]1[NH:18][CH:19]=[NH+:20][C:21]=1[O-:22])(=[O:16])[NH2:15]>N1C=CC=CC=1>[C:1]12([C:11]([O:22][C:21]3[N:20]=[CH:19][NH:18][C:17]=3[C:14](=[O:16])[NH2:15])=[O:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

4

Edukt 2

HCID 989151-Adamantanecarbonyl chlorideHCID 178513830HCID 178513830, Verbindung

Produkt 1

HCID 644655-carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylateAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 1-adamantanecarbonylchloride (2.980 g) in pyridine (26 ml) was added 4-carbamoylimidazolium-5-olate (1.271 g) and the reaction temperature was kept at 40°-43° C. for 4 hours. Unreacted starting material was recovered by filtration (210 mg). The filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (30 ml) and water (30 ml), and stirred at room temperature for 1 hour. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (1.602 g, α form, m.p. 207°-209° C. (dec.)).

Aufarbeitung

  1. filtrationwas recovered by filtration (210 mg)
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate (30 ml) and water (30 ml)
  4. filtrationThe insoluble solid was filtered
  5. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-14894b972b7e4c06a7f63795408aaceb
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04260774

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