Triethylamine → 5-(Azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

HRID 570341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570341
Cl[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)[N:3]=1.C([N:19]([CH2:22][CH3:23])[CH2:20]C)C.Cl.N1CCC1>CC#N>[N:19]1([C:2]2[O:6][N:5]=[C:4]([C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=3)[N:3]=2)[CH2:20][CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12308726Azetidine hydrochlorideHCID 712813525-Chloro-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

Produkt 1

HCID 712815105-(Azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (107) (3.6 g, 15.02 mmol, 1.00 equiv) in CH3CN (40 mL) was added triethylamine (3.03 g, 29.94 mmol) and azetidine hydrochloride (1.68 g, 17.96 mmol). The resulting solution was stirred for 1 hour at room temperature, concentrated under vacuum and purified by prep-HPLC to afford 5-(azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (108) as a white solid. MS m/z 261.1 (M+1)+.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. custompurified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1afaca7cc21848049ce8e3933a835b00
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023839B2

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