Potassium Iodide → 2-[(e)-2-(2-Fluoro-4-trifluoromethyl-phenyl)-vinyl]-4-[4-(4-imidazol-1-ylmethyl-thiazol-2-yl)-phenoxymethyl]-oxazole

HRID 854687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854687
[N:1]1([CH2:6][C:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[S:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:26][C:27]1[N:28]=[C:29]([CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=2[F:44])[O:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:44][C:35]1[CH:36]=[C:37]([C:40]([F:43])([F:41])[F:42])[CH:38]=[CH:39][C:34]=1/[CH:33]=[CH:32]/[C:29]1[O:30][CH:31]=[C:27]([CH2:26][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:9]3[S:10][CH:11]=[C:7]([CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[N:8]=3)=[CH:13][CH:14]=2)[N:28]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 690723654-Chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazoleHCID 1363552334-[4-(Imidazol-1-ylmethyl)-thiazol-2-yl]-phenol

Produkt 1

HCID 694263812-[(e)-2-(2-Fluoro-4-trifluoromethyl-phenyl)-vinyl]-4-[4-(4-imidazol-1-ylmethyl-thiazol-2-yl)-phenoxymethyl]-oxazoleAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 0.129 g (0.50 mmol) 4-[4-(imidazol-1-ylmethyl)-thiazol-2-yl]-phenol and 0.10 g (0.30 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 0.153 g (0.50 mmol) 4-chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazole and 0.083 g (0.50 mmol) potassium iodide were added and stirring at 60° C. continued over night. After evaporation, 15 ml water was added and the mixture extracted with two portions of 15 ml ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and water, dried over sodium sulfate and evaporated to give 241 mg raw material which was purified on silica. Elution with ethyl acetate/methanol 5:1 yielded 88 mg (33%) 2-[(E)-2-(2-Fluoro-4-trifluoromethyl-phenyl)-vinyl]-4-[4-(4-imidazol-1-ylmethyl-thiazol-2-yl)-phenoxymethyl]-oxazole as off-white crystals melting at 133-135° C.

Aufarbeitung

  1. stirringstirring at 60° C.
  2. waitcontinued over night
  3. customAfter evaporation, 15 ml water
  4. additionwas added
  5. extractionthe mixture extracted with two portions of 15 ml ethyl acetate
  6. washThe combined organic layers were washed with 1N sodium hydroxide and water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give 241 mg raw material which
  10. customwas purified on silica
  11. washElution with ethyl acetate/methanol 5:1

Quellen und Nachweise

ORD-Eintrag
ord-6734f8c080734d0c9bb3e586534c60f0
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259262B2

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