Cyclopropanecarbonyl chloride → HCID 178516793, Verbindung

HRID 916259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916259
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:21]([CH:18]1[CH2:20][CH2:19]1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Produkt 1

HCID 178516793HCID 178516793, VerbindungAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (100.0 mg, 0.43 mmol), cyclopropanecarbonylchloride (45.0 mg, 0.43 mmol) and Hunig's base (83.0 mg, 0.64 mmol) in acetonitrile (4 mL) was heated to reflux under argon for 0.5 hr. Cooled to r.t., the reaction mixture was concentrated and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated and the residue was triturated with AcOEt to give a suspension. The solid was filtered to give 2-(cyclopropanecarbonyl-amino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as an oil (113.0 mg, 87.6%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under argon for 0.5 hr
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue was triturated with AcOEt
  8. customto give a suspension
  9. filtrationThe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-608f8ef03d714b5e98e1c7686031c6bf
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268231B2

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