2-Bromopropane → Isopropyl 1-isopropyl-2-bromo-4-methyl-5-imidazolecarboxylate

HRID 1982066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982066
[Br:1][C:2]1[NH:3][C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.N1(C2CCCCCCCCCC2)CCCCCC[CH2:18][CH2:17][CH2:16]N1.Br[CH:37]([CH3:39])[CH3:38]>C1C=CC=CC=1>[CH:17]([N:3]1[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=[C:2]1[Br:1])([CH3:18])[CH3:16].[Br:1][C:2]1[N:6]([CH:37]([CH3:39])[CH3:38])[C:5]([CH3:7])=[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[N:3]=1

Komponenten

6

Edukt 3

HCID 63582-BromopropaneHCID 57346892DiazabicycloundecaneHCID 178432453HCID 178432453, Verbindung

Produkt 2

HCID 13645929Isopropyl 1-isopropyl-2-bromo-4-methyl-5-imidazolecarboxylateAusbeute 70 %HCID 13645930Isopropyl 2-bromo-3-isopropyl-4-methyl-5-imidazolecarboxylateAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 2 g (8.1×10-3 moles) of isopropyl 2-bromo-4-methyl-5-imidazolecarboxylate in 20 ml of benzene was added 1.2 ml (8.2× 10-3 moles) of diazabicycloundecane, followed by 1.0 g (8.1×10-3 moles) of 2-bromopropane. The resulting mixture was heated to reflux overnight, cooled to room temperature and filtered. Concentration in vacuo gave a golden oil. This residue was purified by medium pressure liquid chromatography on silica gel to yield 1.6 g (70%) isopropyl 1-isopropyl-2-bromo-4-methyl-5-imidazolecarboxylate as a yellow oil and 466 milligrams (mg) (20%) of the desired product, isopropyl 2-bromo-3-isopropyl -4-methyl-5-imidazolecarboxylate, also a yellow oil.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationConcentration in vacuo
  5. customgave a golden oil
  6. customThis residue was purified by medium pressure liquid chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7d29a9db82ae44ddb9d4458465192de6
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04595400

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