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

HRID 1615507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615507
[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 microwave irradiation 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 hexane to give the title compound (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. customirradiation at 150° C. for 10 min
  2. concentrationThe reaction mixture was concentrated to small volume until the product
  3. customprecipitated
  4. filtrationThe precipitate was filtered off
  5. washwashed with MeOH and hexane

Quellen und Nachweise

ORD-Eintrag
ord-4dbe7639ecbf46e18f8379dbeae699f0
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765746B2

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