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

HRID 374194

Reaktionsgleichung

Reaktionsgleichung von HRID 374194
[C:1]([N:3]=[C:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)OC)#[N:2].[N+]([O-])(O)=O.[O:16]([CH2:20][CH2:21][NH2:22])[N+:17]([O-:19])=[O:18].C(N(CC)CC)C>CO>[C:1]([NH:3][C:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)=[N:22][CH2:21][CH2:20][O:16][N+:17]([O-:19])=[O:18])#[N:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 102411472-Thiophenecarboximidic acid, N-cyano-, methyl ester

Produkt 1

HCID 10082992N-cyano-N'-(2-nitroxyethyl)-2-thiophenecarboximidamideAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl N-cyano-2-thiophenecarboximidate (0.32 g, 1.9 mmol) was dissolved in methanol (3 ml), and 2-nitroxyethylamine nitrate (0.34 g, 2.0 mmol) and triethylamine (0.20 g, 2.0 mmol) were added. The mixture was stirred at room temperature for 17 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, 25 g) eluting with ethyl acetate. The eluted fractions were concentrated under reduced pressure and crystallized from ethyl acetate-hexane to give the title compound (0.18 g, 0.77 mmol, yield: 40%) as colorless crystals.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washeluting with ethyl acetate
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-7af2253643b74fdb9bbd371bbe2c6e39
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166347

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