Sodium Hydroxide → HCID 68718322, compound

HRID 1441346Notes

Reaction equation

HRID 1441346 reaction equation
[C:1](/[C:4](/[N:7]([CH:12]([CH3:14])[CH3:13])[C:8](=O)[CH2:9][CH3:10])=[CH:5]\[NH2:6])(=[O:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+]>CCO>[CH:12]([N:7]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:5][N:6]=[C:8]1[CH2:9][CH3:10])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 69385700HCID 69385700, compound

Product 1

HCID 68718322HCID 68718322, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

N-[(E)-1-Acetyl-2-aminoethenyl]-N-isopropylpropanamide (Method 7; 373 g, 1.0 eq.) was stirred with sodium hydroxide (1.4 eq.) in EtOH (4 vol.eq.). The reaction was heated to reflux (85° C.) and stirred overnight. Ammonium chloride (2.0 eq.) was then added and this was stirred for 2 hours (the consistency of the reaction changed to a fine precipitate). The reaction was then allowed to cool, the solid was filtered off and discarded, and the solvent was then removed in vacuo. Acetone was then added to the residue, the solid was filtered off and discarded. The solvent was then removed in vacuo. Prep chromatography was then performed by eluting with 5% MeOH/DCM, to leave a brown oil (290 g, 86%). NMR 1.23 (3H, t), 1.43 (6H, d), 2.40 (3H, s), 2.77 (2H, q), 5.0 (1H, b s), 7.87 (1H, s).

Workup

  1. temperatureThe reaction was heated
  2. stirringthis was stirred for 2 hours (the consistency of the reaction
  3. temperatureto cool
  4. filtrationthe solid was filtered off
  5. customthe solvent was then removed in vacuo
  6. additionAcetone was then added to the residue
  7. filtrationthe solid was filtered off
  8. customThe solvent was then removed in vacuo
  9. washby eluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-62ecb2f9364a49c98ce3d469f7f98016
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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