Cyclohexylamine → 3-Cyclohexylaminoacrylonitrile

HRID 2058793Notes

Reaction equation

HRID 2058793 reaction equation
[Na].O[CH:3]=[CH:4][C:5]#[N:6].Cl.[CH:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C1(N)CCCCC1>C(O)C>[CH:8]1([NH:14][CH:3]=[CH:4][C:5]#[N:6])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 2723770Cyclohexylamine hydrochlorideHCID 86738287Sodium 3-hydroxyacrylonitrile

Product 1

HCID 705500993-CyclohexylaminoacrylonitrileYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

32.5 g (0.25 mol) of sodium-3-hydroxyacrylonitrile (content 70%) is added to a suspension of cyclohexylamine hydrochloride (composed of 29.8 g (0.3 mol) of cyclohexylamine and gaseous hydrochloric acid) in 150 ml of ethanol and the mixture is stirred for 24 h at 25° C. After removal of the solid by filtration, and withdrawal of the solvent followed by recrystallization from carbon tetrachloride, 32.1 g (85.6%) of 3-cyclohexylaminoacrylonitrile was obtained.

Workup

  1. customAfter removal of the solid
  2. filtrationby filtration, and withdrawal of the solvent
  3. customfollowed by recrystallization from carbon tetrachloride

Sources & evidence

ORD record
ord-5438d92733664b538aa5924bc2dd3928
Source dataset
uspto-grants-1982_03
Patent number
US04319024

Reaction notes

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