Ethanol, 2-amino-, 1-nitrate, nitrate (1:1) → N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboximidamide

HRID 1588517

Reaktionsgleichung

Reaktionsgleichung von HRID 1588517
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[N+]([O-])(O)=O.[O:19]([CH2:23][CH2:24][NH2:25])[N+:20]([O-:22])=[O:21].C[O-].[Na+]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:25][CH2:24][CH2:23][O:19][N+:20]([O-:22])=[O:21])#[N:2]

Komponenten

5

Edukt 3

HCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl esterHCID 10942334Sodium Methoxide

Produkt 1

HCID 123958N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboximidamideAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 2-nitroxyethylamine nitrate (0.49 g, 2.9 mmol) and sodium methoxide (0.16 g, 2 9 mmol) were added. The mixture was stirred at room temperature for 10 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue was extracted with dichloromethane (50 ml×3). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was crystallized from dichloromethane-diethyl ether to give the title compound (0.48 g, 2.1 mmol, yield: 79%) as colorless needles.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane (50 ml×3)
  3. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrated residue was crystallized from dichloromethane-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4701d9145261472f8d543c94990d622f
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223508

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