Triethylamine → N-cyano-N'-(2-nitroxyethyl)pyrazinecarboximidamide

HRID 374186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 374186
[C:1]([N:3]=[C:4]([C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)OC)#[N:2].[N+]([O-])(O)=O.[O:17]([CH2:21][CH2:22][NH2:23])[N+:18]([O-:20])=[O:19].C(N(CC)CC)C>CO>[C:1]([NH:3][C:4]([C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)=[N:23][CH2:22][CH2:21][O:17][N+:18]([O-:20])=[O:19])#[N:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 10057818Methyl N-cyanopyrazinecarboximidate

Produkt 1

HCID 10331652N-cyano-N'-(2-nitroxyethyl)pyrazinecarboximidamideAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl N-cyanopyrazinecarboximidate (0.49 g, 3.0 mmol) was dissolved in methanol (6 ml), 2-nitroxyethylamine nitrate (1.01 g, 6.0 mmol) and triethylamine (1.01 g, 10.0 mmol) were added. The mixture was stirred at room temperature for 46 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C 200, 30 g) eluting with chloroform-methanol (300:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.18 g, 0.78 mmol, yield: 26%) as colorless crystals.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washeluting with chloroform-methanol (300:1)
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c8529e887c1041cf90a5fa40260146ca
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166347

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