Morpholine → 3-Morpholin-4-yl-2-(morpholin-4-ylcarbonothioyl)acrylonitrile
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]1Participants
4
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 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).
Workup
- customirradiation at 150° C. for 10 min
- concentrationThe reaction mixture was concentrated to small volume until the product
- customprecipitated
- filtrationThe precipitate was filtered off
- washwashed with MeOH and hexane
Sources & evidence
- ORD record
- ord-4dbe7639ecbf46e18f8379dbeae699f0
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765746B2
Reaction notes
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