(R)-3-(4-Bromo-benzyl)-1-(3,5-dichloro-phenyl)-3-methyl-1H-imidazo[1,2-a]imidazol-2-one → (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one

HRID 23839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23839
Br[C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C@@:7]2([CH3:24])[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[N:9]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:8]2=[O:23])=[CH:4][CH:3]=1.[C:27]([Cu])#[N:28]>CN(C=O)C>[C:27]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]2([CH3:24])[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[N:9]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:8]2=[O:23])=[CH:25][CH:26]=1)#[N:28]

Komponenten

4

Edukt 2

HCID 9911635(R)-3-(4-Bromo-benzyl)-1-(3,5-dichloro-phenyl)-3-methyl-1H-imidazo[1,2-a]imidazol-2-oneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 59923742(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-oneAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

(R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-α]-imidazol-2-one (13.5 g, 29.9 mmol) was dissolved in anhydrous DMF (70 mL) and CuCN (3.22 g, 35.9 mmol) was added. The reaction mixture was heated to 140° C. under argon for 40 h. When the reaction was complete, the solvent was removed under reduced pressure and the residue was diluted with CH2Cl2. The organic solution was washed four times alternately with 5% aqueous pyridine then water. The organic layer was dried over Na2SO4 and filtered through a diatomaceous earth pad. The filtrate was concentrated and purified by silica gel column chromatography using a mixture of CH2Cl2-hexane (10:1) as an eluent to afford 9.19 g of (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was diluted with CH2Cl2
  3. washThe organic solution was washed four times alternately with 5% aqueous pyridine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered through a diatomaceous earth pad
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. additiona mixture of CH2Cl2-hexane (10:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-1ee585fcc3c146aba734715a5c383c6d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852748B1

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