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

HRID 572609Notes

Reaction equation

HRID 572609 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b22ae71404fa4de6a01bf77a51ce556d
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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