Sodium Hydroxide → HCID 68686772, compound

HRID 1441349Notes

Reaction equation

HRID 1441349 reaction equation
[C:1](/[C:4](/[N:7]([CH2:13][CH3:14])[C:8](=O)[CH2:9][CH2:10][CH3:11])=[CH:5]\[NH2:6])(=[O:3])[CH3:2].[OH-].[Na+].[NH4+].[Cl-]>CCO>[CH2:13]([N:7]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:5][N:6]=[C:8]1[CH2:9][CH2:10][CH3:11])[CH3:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86613528HCID 86613528, compound

Product 1

HCID 68686772HCID 68686772, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[(E)-1-acetyl-2-aminoethenyl]-N-ethylbutanamide (Method 11; 33.9 g, 171 mM) and NaOH (8.2 g, 205 mM) in EtOH (400 ml) was heated under reflux for 4 hours. NH4Cl (11.9 g, 222 mM) was added to the hot solution, which was allowed to cool and stir for 48 hours. The reaction mixture was filtered and the solution was evaporated. The residue was taken into ether and filtered again. The solution was evaporated to give the title compound as a yellow oil (30.55 g, 74%). NMR (300 Mz, DMS0-d6): 0.92 (t, 3H), 1.17 (t, 3H), 1.70 (sext, 2H), 2.37 (s, 3H), 2.64 (t, 2H), 4.23 (q, 2H), 7.83 (s, 1H); m/z 181.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureto cool
  3. filtrationThe reaction mixture was filtered
  4. customthe solution was evaporated
  5. filtrationfiltered again
  6. customThe solution was evaporated

Sources & evidence

ORD record
ord-88076eca1ab64d7ca3eb04a14a72ae12
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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