3-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester → N-cyano-N'-(3-benzyloxybenzyl)-3-pyridinecarboximidamide

HRID 374157

Reaktionsgleichung

Reaktionsgleichung von HRID 374157
[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].[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:27][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:24]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl esterHCID 11009288(3-(Benzyloxy)phenyl)methanamine

Produkt 1

HCID 19734575N-cyano-N'-(3-benzyloxybenzyl)-3-pyridinecarboximidamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Isopropyl N-cyano-3-pyridinecarboximidate (0.30 g, 1.6 mmol) was dissolved in methanol (10 ml), and 3-benzyloxybenzylamine (0.41 g, 1.9 mmol) was added. The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The concentrated residue was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g). Elution with chloroform-methanol (100:1) was conducted, the eluted fractions were concentrated under reduced pressure, and the concentrated residue thus obtained was crystallized from methanol-diethyl ether to give the title compound (0.48 g, 1.4 mmol, yield: 88%) as colorless crystals.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. washElution with chloroform-methanol (100:1)
  3. concentrationthe eluted fractions were concentrated under reduced pressure
  4. customthe concentrated residue thus obtained
  5. customwas crystallized from methanol-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d3acef40ec88470ebf6918045d2ff673
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166347

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