Sodium Iodide → Morpholine, 4-(2-(2-nitro-1H-imidazol-1-yl)ethyl)-

HRID 1468811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468811
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[I-].[Na+].C[O-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[N:5]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 107012-NitroimidazoleHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Produkt 1

HCID 100573Morpholine, 4-(2-(2-nitro-1H-imidazol-1-yl)ethyl)-Ausbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Nitroimidazole (0.55 g, 4.86 mmol), 4-(2-chloroethyl)morpholine hydrochloride (0.90 g, 4.86 mmol), sodium iodide (0.18 g, 1.21 mmol) and sodium methoxide (0.59 g, 10.0 mmol) are dissolved in DMF (25 mL). The mixture is heated at 100° C. under a nitrogen atmosphere for 14 h. The reaction mixture is cooled and solvent removed in vacuo. The residue is partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (aq.) (30 mL). The aqueous layer is extracted with ethyl acetate (4×30 mL). The organic layers are combined, dried (MgSO4) and solvent removed in vacuo. The solid residue is purified by column chromatography, eluting with 3% methanol in dichloromethane to give a yellow oil (638 mg, 58%). 1H-NMR (400 MHz, d6-DMSO) =2.39-2.45 (m, 4H), 2.66 (t, 2H, J=6 Hz), 3.52 (t, 4H, J=4.8 Hz), 4.52-4.54 (t, 2H, J=6 Hz), 7.19 (s, 1H, Har), 7.68 (s, 1H, Har).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customsolvent removed in vacuo
  3. customThe residue is partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (aq.) (30 mL)
  4. extractionThe aqueous layer is extracted with ethyl acetate (4×30 mL)
  5. dry with materialdried (MgSO4) and solvent
  6. customremoved in vacuo
  7. customThe solid residue is purified by column chromatography
  8. washeluting with 3% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-093dbf4da7b94775bfa460898e1b990f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006237B2

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