Diethyl (ethoxymethylene)malonate → HCID 178469787, compound

HRID 574659

Reaction equation

HRID 574659 reaction equation
[Na].[CH2:2]([O:9][CH2:10][C:11]([NH2:13])=[NH:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>CCO>[CH2:2]([O:9][CH2:10][C:11]1[N:13]=[C:17]([OH:16])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][N:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 4164062-PhenylmethoxyethanimidamideHCID 5360545Sodium

Product 1

HCID 178469787HCID 178469787, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (4.6 g, 200 mmol) was added to EtOH (500 mL) and the mixture was stirred until a clear solution was obtained. Then, step B product, 2-c, (20.1 g, 100 mmol) and diethyl 2-(ethoxymethylene)malonate (21.6 g, 100 mmol) were added to the clear mixture, respectively. The reaction mixture was refluxed overnight and then concentrated under vacuum, washed with EA. The wet cake was then dried to afford compound 2-d (40.0 g, crude). LC-MS: (M+H)+ 289. The crude was directly used to next step without further purification.

Workup

  1. customwas obtained
  2. temperatureThe reaction mixture was refluxed overnight
  3. concentrationconcentrated under vacuum
  4. washwashed with EA
  5. customThe wet cake was then dried
  6. customto afford compound 2-d (40.0 g, crude)
  7. customThe crude was directly used to next step without further purification

Sources & evidence

ORD record
ord-941e7dbe208c45f5adc496c3dd093870
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Linked notes

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