Diethyl (ethoxymethylene)malonate → 1,3-Diethyl 2-[[(4-ethoxyphenyl)amino]methylene]propanedioate

HRID 1276006Notes

Reaction equation

HRID 1276006 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1.C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>CCCCCC>[CH2:19]([O:18][C:16](=[O:17])[C:15](=[CH:14][NH:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH:6]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:20]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 90764-Ethoxyaniline

Product 1

HCID 22675511,3-Diethyl 2-[[(4-ethoxyphenyl)amino]methylene]propanedioateYield 84.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 41.15 g (0.3 Mol) of p-phenetidine in 90 ml of hexane, 64.9 g (0.3 Mol) of diethyl ethoxymethylenemalonate was added dropwise with stirring at room temperature. After an additional hour of stirring at room temperature, the reaction mixture was cooled with an ice bath and the product crystallized spontaneously. The crude solid material was isolated by filtration and washed with hexane to give 78.3 g of the title product; white solid melting at 55-56° C. UV 329 nm (E=802).

Workup

  1. stirringAfter an additional hour of stirring at room temperature
  2. temperaturethe reaction mixture was cooled with an ice bath
  3. customthe product crystallized spontaneously
  4. customThe crude solid material was isolated by filtration
  5. washwashed with hexane

Sources & evidence

ORD record
ord-3b5d9426d44343ac88132326ee35b793
Source dataset
uspto-grants-2000_12
Patent number
US06165451

Reaction notes

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