Carbon Disulfide → Methyl 2-butyl-1-[[2'-(2,5-dihydro-5-thioxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazol-7-carboxylate

HRID 1870930

Reaktionsgleichung

Reaktionsgleichung von HRID 1870930
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23](=[NH:29])[NH:24][O:25][C:26](=O)C)=[CH:13][CH:12]=2)[C:8]2[C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C(=S)=[S:39].[H-].[Na+]>CN(C=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:24][O:25][C:26](=[S:39])[N:29]=3)=[CH:13][CH:12]=2)[C:8]2[C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 178418641HCID 178418641, Verbindung

Produkt 1

HCID 10649000Methyl 2-butyl-1-[[2'-(2,5-dihydro-5-thioxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazol-7-carboxylateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of methyl 2-butyl-1-[[2'-(acetoxycarbamimidoyl)biphenyl-4-yl)methyl]benzimidazole-7-carboxylate (2.0 g) and CS2 (1.5 g) in DMF (12 ml) was added sodium hydride (60% in oil, 0.56 g) during a period of 10 minutes and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-water and the pH of the solution was adjusted to 3. The mixture was extracted with ethylacetate and the extract was washed with water, dried, and concentrated to dryness. The residue was crystallized from chloroform-methanol to afford pale yellow prisms (0.64 g, 32%).

Aufarbeitung

  1. extractionThe mixture was extracted with ethylacetate
  2. washthe extract was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue was crystallized from chloroform-methanol

Quellen und Nachweise

ORD-Eintrag
ord-1b42b76dab734c20aee1e4bac7af99c9
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100252

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