Acetic Acid → n,n-Bis(2-cyanoethyl)octadecylamine
Reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5](O)[CH3:6].[CH2:8]([NH2:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].O.[NH3:28].[C:29](O)(=O)C>O>[C:29]([CH2:5][CH2:6][N:26]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH2:2][C:1]#[N:4])#[N:28]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 77 °C
Procedure
40.2 g of acrylonitrile was added dropwise to an ethanol solution (150 ml) of 41.7 g of stearylamine at room temperature over 0.5 hours, 22.5 g of acetic acid was added dropwise thereto over 0.5 hours, and then stirred at 77° C. for 10 hours. After standing to cool to room temperature, the mixed solution was added with 200 ml of water and 22.8 g of 28% ammonia water, and extracted with 500 ml of ethyl acetate. The organic layer was separated from the solution, washed twice with 100 ml of water and 50 ml of saturated saline, dried over anhydrous magnesium sulfate. After distilling off the solvent, the concentrated residue was recrystallized using isopropyl alcohol as a solvent to obtain 42.4 g of a target compound as a white solid.
Workup
- temperatureto cool to room temperature
- extractionextracted with 500 ml of ethyl acetate
- customThe organic layer was separated from the solution
- washwashed twice with 100 ml of water and 50 ml of saturated saline
- dry with materialdried over anhydrous magnesium sulfate
- distillationAfter distilling off the solvent
- customthe concentrated residue was recrystallized
Sources & evidence
- ORD record
- ord-d2fb62cec9164f48957a19e44449b09d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08830811B2
Reaction notes
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