Cesium carbonate → Ethyl2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-propionate

HRID 660871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660871
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[NH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionateHCID 580118325-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

Produkt 1

HCID 58011824Ethyl2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

500 mg (2.13 mmol) of 5-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one from Example 118A are dissolved in 5 ml acetonitrile and treated with 386 mg (2.13 mmol) of ethyl 2-bromopropionate and 1388 mg (4.26 mmol) of caesium carbonate. The mixture is stirred under reflux overnight. It is then concentrated, the residue is partitioned between dichloromethane and water, the organic phase is separated, and this is dried over sodium sulphate and again concentrated. The crude product is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1→100:1) and thus yields 338 mg (45% of theory) of the target compound.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. concentrationIt is then concentrated
  3. customthe residue is partitioned between dichloromethane and water
  4. customthe organic phase is separated
  5. dry with materialthis is dried over sodium sulphate
  6. concentrationagain concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (eluent

Quellen und Nachweise

ORD-Eintrag
ord-303ae6f527f44bcbabf0f85dd680a8c5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084481B2

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