Dimethylformamide → Bis-(2-chloroethyl){4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}amine

HRID 2407504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407504
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:30]=[CH:29][C:20]([CH2:21][N:22]([CH2:26]CO)[CH2:23][CH2:24]O)=[CH:19][CH:18]=3)[N:13]=2)[CH:9]=[CH:8][C:7]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN(C)C=O.Cl[CH2:43][Cl:44]>>[Cl:3][CH2:24][CH2:23][N:22]([CH2:26][CH2:43][Cl:44])[CH2:21][C:20]1[CH:29]=[CH:30][C:17]([C:14]2[N:13]=[C:12]([C:10]3[CH:9]=[CH:8][C:7]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:6]([F:5])[CH:11]=3)[O:16][N:15]=2)=[CH:18][CH:19]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 595094342-[{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)amino]ethanol

Produkt 1

HCID 59509478Bis-(2-chloroethyl){4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}amine

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Thionyl chloride (52 mL, 0.716 mol) is added drop wise to a stirred solution of 2-[{4-[5-(2-fluoro-biphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)-amino]ethanol (31 g, 0.0715 mol) in dichloromethane (150 mL) at 0° C. N,N-Dimethylformamide (2 mL) is added and the reaction mixture is heated at 80° C. for 1 h. Excess thionyl chloride is removed under reduced pressure and the residue is made alkaline (pH ˜9) by the addition of an aqueous sodium hydroxide solution (4N, 150 mL) at room temperature. The aqueous layer is extracted with ethyl acetate (2×100 mL) and combined organic layers are dried over sodium sulphate. Removal of solvent under reduced pressure gives a viscous liquid, which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 7:3) to give bis-(2-chloroethyl){4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}amine.

Aufarbeitung

  1. customExcess thionyl chloride is removed under reduced pressure
  2. additionby the addition of an aqueous sodium hydroxide solution (4N, 150 mL) at room temperature
  3. extractionThe aqueous layer is extracted with ethyl acetate (2×100 mL)
  4. dry with materialare dried over sodium sulphate
  5. customRemoval of solvent under reduced pressure
  6. customgives a viscous liquid, which
  7. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-04285bb8b1ea4d02a11babda30274159
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809539B2

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