Stannous chloride dihydrate → 5-(5-(Azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylaniline

HRID 570342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570342
[N:1]1([C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-])=O)[CH:11]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.O.O.Cl[Sn]Cl>C(O)C>[N:1]1([C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH:11]=3)[NH2:17])[N:6]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 712815105-(Azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

Produkt 1

HCID 866774565-(5-(Azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylanilineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-(azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (108) (1.4 g, 5.38 mmol) in ethanol (25 mL) was added SnCl2.2H2O (6.07 g, 26.90 mmol). The resulting solution was stirred for 20 min at reflux then cooled to room temperature and concentrated under vacuum. The residue was poured into saturated sodium hydroxide (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×250 mL), dried over anhydrous sodium sulfate, concentrated under vacuum and purified by flash chromatography (PE/EA=10:1) to afford 5-(5-(azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (109) (0.8 g, 65% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.28-7.36 (m, 2H), 7.12 (d, J=7.8 Hz, 1H), 4.32 (t, J=7.5 Hz, 4H), 3.69 (brs, 2H), 2.47-2.57 (m, 2H), 2.21 (s, 3H). MS m/z 231.1 (M+1)+.

Aufarbeitung

  1. temperatureat reflux
  2. concentrationconcentrated under vacuum
  3. additionThe residue was poured into saturated sodium hydroxide (50 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic layers were washed with brine (3×250 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. custompurified by flash chromatography (PE/EA=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-4461e0029b324fcdb2c23058864ffa7e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023839B2

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