Acetic Acid → 3-(Diethylamino)prop-2-enenitrile

HRID 2058792Notes

Reaction equation

HRID 2058792 reaction equation
[Na].O[CH:3]=[CH:4][C:5]#[N:6].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].C(O)(=O)C>C(#N)C>[CH2:7]([N:9]([CH2:10][CH3:11])[CH:3]=[CH:4][C:5]#[N:6])[CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8021DiethylamineHCID 86738287Sodium 3-hydroxyacrylonitrile

Product 1

HCID 540401103-(Diethylamino)prop-2-enenitrileYield 63.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

32.5 g (0.25 mol) of sodium-3-hydroxyacrylonitrile (content 70%) is added to a solution of 25.6 g (0.35 mol) of diethylamine, 21.0 g (0.35 mol) of acetic acid and 150 ml of acetonitrile, and the mixture is stirred for 16 h at 25° C. After working up as in Example 50, 19.7 g of 3-diethylaminoacrylonitrile was obtained (63.6%).

Sources & evidence

ORD record
ord-790649635e9949e3bf62f63ea2d5c65b
Source dataset
uspto-grants-1982_03
Patent number
US04319024

Reaction notes

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