Dimethylformamide → 2-bromo-1-(2-butynyl)-1H-imidazole-4,5-dicarbonitrile

HRID 501445

Reaktionsgleichung

Reaktionsgleichung von HRID 501445
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:13][C:14]#[C:15][CH3:16].[Br:17][C:18]1[NH:19][C:20]([C:25]#[N:26])=[C:21]([C:23]#[N:24])[N:22]=1>O.C(OCC)(=O)C>[Br:17][C:18]1[N:19]([CH2:13][C:14]#[C:15][CH3:16])[C:20]([C:25]#[N:26])=[C:21]([C:23]#[N:24])[N:22]=1

Komponenten

7

Edukt 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 27791482-bromo-1H-imidazole-4,5-dicarbonitrile

Produkt 1

HCID 230708722-bromo-1-(2-butynyl)-1H-imidazole-4,5-dicarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

69.8 g of potassium carbonate and 50 ml N,N-dimethylformamide solution of 74 ml of 1-bromo-2-butyne were added to a 520 ml N,N-dimethylformamide solution of 90.6 g of 2-bromo-1H-imidazole-4,5-dicarbonitrile [CAS No 50847-09-1], and the mixture was heated at 50° C. for 8 hours. 1 L of ethyl acetate and 500 ml of water were added to the solution, and the organic layer was washed twice with 500 ml of water and then with 500 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 48.0 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (1:4).

Aufarbeitung

  1. washthe organic layer was washed twice with 500 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-56faf7657c0340b58029531e17688cc7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772226B2

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