Methyl triflate → 1,5-Dimethyl-2-(4-trifluoromethylphenyl)imidazole

HRID 22242

Reaktionsgleichung

Reaktionsgleichung von HRID 22242
F[C:2](F)(F)S(OC)(=O)=O.[F:10][C:11]([F:21])([F:20])[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[CH2:22]([NH2:25])[C:23]#[CH:24].[OH-].[Na+]>C(#N)C.C(Cl)Cl>[CH3:2][N:17]1[C:23]([CH3:24])=[CH:22][N:25]=[C:16]1[C:15]1[CH:18]=[CH:19][C:12]([C:11]([F:20])([F:21])[F:10])=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 9526Methyl triflateHCID 14798Sodium HydroxideHCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 239041Propargylamine

Produkt 1

HCID 194303261,5-Dimethyl-2-(4-trifluoromethylphenyl)imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of methyl trifluoromethanesulfonate (3.3 ml) and p-trifluoromethylbenzonitrile (5.17 g) was heated at 65° C. for 31/2 hours, then cooled to 5° C. The mixture was then dissolved in 10 ml of acetonitrile, and 2 ml of propargylamine in 10 ml of acetonitrile was added. The mixture was stirred at room temperature for 16 hours, then cooled to 5° C. and 3 ml of concentrated sodium hydroxide added (about 1 equivalent), followed by 40 ml of methylene chloride. The organic layer was separated, the solvent evaporated under reduced pressure, and 50 ml of toluene added. The mixture was refluxed for 3 hours, cooled, the solvent evaporated under reduced pressure, and the residue recrystallized from isopropyl ether, to yield 4.6 g of 1,5-dimethyl-2-(4-trifluoromethylphenyl)imidazole, a compound of Formula (6), m.p. 130° C.

Aufarbeitung

  1. temperaturecooled to 5° C
  2. temperaturecooled to 5° C.
  3. customThe organic layer was separated
  4. customthe solvent evaporated under reduced pressure, and 50 ml of toluene
  5. additionadded
  6. temperatureThe mixture was refluxed for 3 hours
  7. temperaturecooled
  8. customthe solvent evaporated under reduced pressure
  9. customthe residue recrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8a361d1bf92d440e8c76e29a51b3f5f0
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428037

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