But-2-yn-1-amine → HCID 178449099, Verbindung

HRID 27381

Reaktionsgleichung

Reaktionsgleichung von HRID 27381
[N+:1]([CH:4]=[C:5](SC)[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[CH3:16])([O-:3])=[O:2].[CH2:19]([NH2:23])[C:20]#[C:21][CH3:22]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:23][CH2:19][C:20]#[C:21][CH3:22])[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[CH3:16])([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 12599998But-2-yn-1-amineHCID 178503826HCID 178503826, Verbindung

Produkt 1

HCID 178449099HCID 178449099, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1-nitro-2-methylthio-2-{2-[(4-methyl-1H-imidazol-5-yl)methylthio]ethylamino}ethylene (2.25 g, 7.8 mmole) and 2-butyn-1-amine (2.16 g, 31.2 mmole) in acetonitrile (35 ml) was stirred under a positive pressure of nitrogen at reflux temperature for 7 hours and at room temperature for 15 hours. The solvent was removed by evaporation under reduced pressure, and the residue placed on silica gel and chromatographed by gradient elution using methylene chloride-methanol. The appropriate fractions yielded 1.93 g (80%) of the title product from acetonitrile. Recrystallization from isopropyl alcohol gave the product with mp 147.5°-151°.

Aufarbeitung

  1. temperatureat reflux temperature for 7 hours
  2. customThe solvent was removed by evaporation under reduced pressure
  3. customchromatographed by gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-cb5192f8f86244b28cb277a0844b27e9
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221737

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