Potassium Carbonate → 4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

HRID 488736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488736
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C:8]2([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+]>C1(C)C(C)=CC=CC=1>[Cl:26][C:21]1[CH:20]=[C:19]([N:18]2[C:9]3=[CH:10][CH2:11][CH2:12][CH2:13][C:8]3([CH2:7][C:6]3[CH:27]=[CH:28][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[NH:15][C:16]2=[O:17])[CH:24]=[C:23]([Cl:25])[CH:22]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 222680621-[1-(4-Cyano-benzyl)-2-oxocyclohexyl]-3-(3,5-dichlorophenyl)-urea

Produkt 1

HCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrileAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A suspension of 1-[1-(4-cyano-benzyl)-2-oxocyclohexyl]-3-(3,5-dichlorophenyl)-urea (3.7 g) (0.009 mol), K2CO3 (2.6 g) (2.1 eq) and molecular sieves 4A (10 g) in xylene (500 ml) was refluxed 16 h. After cooling, the reaction mixture was filtered on paper, concentrated in vacuo, and the residue purified on SiO2 chromatography (eluent EtOAc/cyclohexane-3/7) to yield 4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (1.8 g) as a white solid. 1H NMR (CDCl3): 7.6 (2H, d), 7.35 (2H, d), 7.15 (1H, m), 6.95 (2H, m), 5.65 (1H, bs), 4.95 (1H, m), 3.1 (1H, d), 2.9 (1H, d), 2.5-2.1 (2H, m), 2.1-1.65 (4H, m).

Aufarbeitung

  1. temperaturewas refluxed 16 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered on paper
  4. concentrationconcentrated in vacuo
  5. customthe residue purified on SiO2 chromatography (eluent EtOAc/cyclohexane-3/7)

Quellen und Nachweise

ORD-Eintrag
ord-e9ba7d29de1d47e2b0a0db1fa83e4bcb
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974815B2

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