Potassium Iodide → 1-[4-(4-{2-[2-(4-Trifluoromethylsulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

HRID 1271396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271396
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[O:6][CH:7]=1.[N:21]1([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[CH:25]=[CH:24][N:23]=[N:22]1.[I-].[K+].C[O-].[Na+]>CO>[F:18][C:17]([S:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[CH:8][C:5]2[O:6][CH:7]=[C:3]([CH2:2][O:36][C:33]3[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)=[CH:31][CH:32]=3)[N:4]=2)=[CH:11][CH:12]=1)([F:20])[F:19]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 691129774-Chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazole

Produkt 1

HCID 692918251-[4-(4-{2-[2-(4-Trifluoromethylsulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.32 g (1.00 mmol) 4-Chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazole, 0.217 g (1.00 mmol) 4-(4-[1,2,3]Triazol-1-yl-butyl)-phenol, 0.166 g (1.00 mmol) potassium iodide and 0.191 ml (1.00 mmol) of sodium methylate (30% in methanol) were added to 50.0 ml methanol and heated to reflux for 16 h. After removal of solvent and partitioning of the residue between 50 ml ethyl acetate and 15 ml water, the organic phase was washed with 10 ml water, 10 ml 0.1 N NaOH and twice 15 ml water, and dried over sodium sulfate. The solution was concentrated until crystallisation of the product started. After leaving for 1 h at room temperature the precipitate was isolated, washed with ether and dried at 40° C. in vacuo. Yield 0.11 g (18%) 1-[4-(4-{2-[2-(4-Trifluoromethylsulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole, m.p. 144–145° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customAfter removal of solvent
  4. custompartitioning of the residue between 50 ml ethyl acetate and 15 ml water
  5. washthe organic phase was washed with 10 ml water, 10 ml 0.1 N NaOH and twice 15 ml water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solution was concentrated until crystallisation of the product
  8. customAfter leaving for 1 h at room temperature the precipitate
  9. customwas isolated
  10. washwashed with ether
  11. customdried at 40° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9abd7797a62447028bd75506aeb7c04f
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205325B2

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