Diethyl (ethoxymethylene)malonate → HCID 67954621, compound

HRID 1846385Notes

Reaction equation

HRID 1846385 reaction equation
[C:1]1([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[NH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>C(O)C>[O:19]=[C:20]1[N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:10][CH:27]=[C:21]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 178512092HCID 178512092, compound2×

Product 1

HCID 67954621HCID 67954621, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-(phenylmethyl)-benzenecarboximidamide (i.e. the product from Step A) (2.54 g, 12.1 mmol) in ethanol (15 mL) was added diethyl ethoxymethylenemalonate (2.61 g, 12.1 mmol), and the reaction mixture was heated to reflux for 24 h. The reaction mixture was then allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product as a white solid (2.9 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7e56a44b8cbe477fa2270bc53329f797
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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