Aziridine → 3-(Aziridin-1-yl)-2,6-dinitrobenzamide

HRID 1058512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058512
Cl[C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[NH:17]1[CH2:19][CH2:18]1>CCOC(C)=O>[N:17]1([C:2]2[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[C:5]([NH2:7])=[O:6])[CH2:19][CH2:18]1

Komponenten

4

Edukt 2

HCID 9033AziridineHCID 186681703-Chloro-2,6-dinitrobenzamide

Produkt 1

HCID 101312063-(Aziridin-1-yl)-2,6-dinitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of 3-chloro-2,6-dinitrobenzamide (Palmer et al., J. Med. Chem., 1996, 29, 2518-2528) (0.50 g, 2.04 mmol) and aziridine (1.00 g, 0.023 mol) in EtOAc (80 mL) was stirred at room temperature for 18 h. After washing with water the solution was dried over Na2SO4 and concentrated under reduced pressure to ca. 20 mL. Petroleum ether was added until a slight cloudiness persisted and the solution was chilled at −20° C. to give 13: mp 206-210° C. (dec.); 1H NM [(CD3)2SO] δ8.26 (br s, 1H, CONH), 8.24 (d, J=9.0 Hz, 1H, H-5), 7.92 (br s, 1H, CONH), 7.44 (d, J=9.0 Hz, 1H, H-4), 2.35 (s, 4H, aziridine-H); 13C NMR δ162.67 (s), 150.63 (s), 141.82 (s), 139.32 (s), 128.17 (s), 127.77 (d), 123.31 (d), 28.41 (t). Anal. Calcd for C9H8N4O5; C, 42.86;H, 3.20; N, 22.22. Found: C, 42.97;H, 3.15; N, 22.32%.

Aufarbeitung

  1. washAfter washing with water the solution
  2. dry with materialwas dried over Na2SO4
  3. concentrationconcentrated under reduced pressure to ca. 20 mL
  4. additionPetroleum ether was added until a slight cloudiness

Quellen und Nachweise

ORD-Eintrag
ord-03051f21167c493fb2f1889020a73476
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06517836B1

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