Methyl Methanesulfonate → 1-Methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridinium methanesulfonate

HRID 53214

Reaktionsgleichung

Reaktionsgleichung von HRID 53214
[F:1][C:2]([F:27])([F:26])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:23]=[C:22]([CH3:24])[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:10]([CH3:25])[CH:9]=2)[N:4]=1.[CH3:28][S:29]([O:32]C)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:28][S:29]([O-:32])(=[O:31])=[O:30].[CH3:28][N+:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][CH2:14][CH2:13][O:12][C:11]2[C:22]([CH3:24])=[CH:23][C:8]([C:5]3[N:4]=[C:3]([C:2]([F:1])([F:26])[F:27])[O:7][N:6]=3)=[CH:9][C:10]=2[CH3:25])[CH:17]=1

Komponenten

4

Edukt 2

HCID 4156Methyl Methanesulfonate2×HCID 190820123-[3-[4-(5-Trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine

Produkt 1

HCID 190820401-Methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridinium methanesulfonateAusbeute 157 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine (1 g, 2.6 mmol, 1.1 eq) in 10 ml of methylene chloride was added methyl methanesulfonate (0.32 g, 2.9 mmol) and the mixture was gently refluxed overnight. After adding 0.5 eq of methyl methanesulfonate, the mixture was allowed to reflux an additional 24 h. The mixture was concentrated in vacuo and a solid residue was washed with ether to afford 1.11 g (85.3%) of 1-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridinium methanesulfonate, as a white powder.

Aufarbeitung

  1. temperatureto reflux an additional 24 h
  2. concentrationThe mixture was concentrated in vacuo
  3. washa solid residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-4137d816472d4cdeb63c64978c7718ac
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618821

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