Morpholine → 3-Morpholin-4-yl-2-(morpholin-4-ylcarbonothioyl)acrylonitrile

HRID 572609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572609
[N:1]1([C:7](=[S:11])[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:12](OC(OCC)OCC)C.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[N:22]1([CH:12]=[C:8]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[S:11])[C:9]#[N:10])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Komponenten

4

Edukt 3

HCID 8083MorpholineHCID 31214Ethyl orthoformateHCID 451589413-Morpholin-4-yl-3-thioxopropanenitrile

Produkt 1

HCID 852399573-Morpholin-4-yl-2-(morpholin-4-ylcarbonothioyl)acrylonitrileAusbeute 83 %

Versuchsvorschrift

To a solution of 3-morpholin-4-yl-3-thioxopropanenitrile (0.1 g, 0.59 mmol) in triethylorthoformate (0.245 mL, 1.48 mmol) was added morpholine (0.064 mL, 0.73 mmol). The reaction mixture was subjected to MWI at 150° C. for 10 min. The reaction mixture was concentrated to small volume until the product precipitated. The precipitate was filtered off, washed with MeOH and isohexane to give 3-morpholin-4-yl-2-(morpholin-4-ylcarbonothioyl)acrylonitrile (0.13 g, 83%). LCMS: (AA) ES+ 268.2. 1H NMR (400 MHz, d6-DMSO) δ: 3.96 m, 4H) and 3.67-3.78 (m, 12H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to small volume until the product
  2. customprecipitated
  3. filtrationThe precipitate was filtered off
  4. washwashed with MeOH and isohexane

Quellen und Nachweise

ORD-Eintrag
ord-b22ae71404fa4de6a01bf77a51ce556d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029411B2

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