Water → 2-Ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazole

HRID 1480018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480018
F[B-](F)(F)F.C([O+:8]([CH2:11][CH3:12])[CH2:9]C)C.[CH3:13][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)C(=O)[NH:16][CH:15]=1.O.[OH-].[Na+]>C(Cl)Cl>[CH2:11]([O:8][C:9]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:14]([CH3:13])=[CH:15][N:16]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723982Triethyloxonium tetrafluoroborateHCID 814460105-Methyl-1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2H-imidazol-2-one

Produkt 1

HCID 1213937382-Ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazoleAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of triethyloxonium tetrafluoroborate (9.0 g, 47 mmol) in DCM (62 mL) was added to a stirred solution of 5-methyl-1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2H-imidazol-2-one (9.0 g, 37 mmol) in DCM (124 mL) under a nitrogen atmosphere. The solution was stirred at RT for 2.5 h then treated with water (50 mL) then 1 M sodium hydroxide (50 mL). The phases were partitioned. The aqueous phase was washed with DCM (2×50 mL). The combined organic phase was dried (sodium sulfate). The solution of the crude product was filtered through 2×50 g flash SCX 2 cartridges. Each cartridge was rinsed with 10% methanol in DCM (100 mL) then the product fraction was eluted with 2M methanolic ammonia solution (100 mL). The fractions recovered with methanolic ammonia were combined and concentrated in vacuo to afford the title compound (7.92 g) as a brown solid.

Aufarbeitung

  1. customThe phases were partitioned
  2. washThe aqueous phase was washed with DCM (2×50 mL)
  3. dry with materialThe combined organic phase was dried (sodium sulfate)
  4. filtrationThe solution of the crude product was filtered through 2×50 g flash SCX 2 cartridges
  5. washEach cartridge was rinsed with 10% methanol in DCM (100 mL)
  6. washthe product fraction was eluted with 2M methanolic ammonia solution (100 mL)
  7. customThe fractions recovered with methanolic ammonia
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-40d6001110db48b39121332135f4da66
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409870B2

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