Water → 5-(3-Chloro-4-isobutylphenyl)-3-(4-chloromethylphenyl)-[1,2,4]-oxadiazole

HRID 1777361

Reaktionsgleichung

S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:12]=[C:13]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32]O)=[CH:28][CH:27]=3)[N:22]=2)[CH:14]=[CH:15][C:16]=1[CH2:17][CH:18]([CH3:20])[CH3:19].O>ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][Cl:3])=[CH:28][CH:27]=3)[N:22]=2)[CH:14]=[CH:15][C:16]=1[CH2:17][CH:18]([CH3:20])[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 42.5 °C

Versuchsvorschrift

Thionyl chloride (3.1 mL, 0.043 mol) and N,N-dimethylformamide (0.2 mL) are added to a stirred solution of {4-[5-(3-chloro-4-isobutylphenyl)-[1,2,4]-oxadiazol-3-yl]-phenyl}methanol (4.9 g, 0.0143 mol) in dichloromethane (30 mL) at 0° C. The reaction mixture is heated at 40-45° C. and is stirred at this temperature for 30 minutes. It is then cooled to 0-5° C. temperature, treated with demineralized water (3 mL) and neutralized with caustic lye to adjust the pH to 8-9. Finally it is extracted with dichloromethane (2×20 mL) and the combined extract is dried over sodium sulfate. Removal of solvent under reduced pressure gives 5-(3-chloro-4-isobutylphenyl)-3-(4-chloromethylphenyl)-[1,2,4]-oxadiazole.

Aufarbeitung

temperatureIt is then cooled to 0-5° C. temperature
extractionFinally it is extracted with dichloromethane (2×20 mL)
extractionthe combined extract
dry with materialis dried over sodium sulfate
customRemoval of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-ac06aa25c4f0488bac528b950799bc83
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09266867B2

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