Diethyl (ethoxymethylene)malonate → 2-((4-Methoxy-phenylamino)-methylene)-malonic acid diethyl ester

HRID 747487Notes

Reaction equation

HRID 747487 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7732P-Anisidine

Product 1

HCID 6189812-((4-Methoxy-phenylamino)-methylene)-malonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
92.5 °C

Procedure

3.5 kg of p-anisidine are added to 6.25 kg of diethyl ethoxymethylenemalonate at 14° C., over 85 minutes without cooling of the reaction mass. At the end of addition, the temperature has reached 59° C. The temperature is kept at 59° C. for 30 minutes, and the reaction medium is then heated to 90-95° C. and kept at this temperature for 1 hour. The ethanol formed is then removed by distillation at atmospheric pressure and then under 250 mbar. After cooling to 45° C., 8.4 kg of diethyl 2-[(4-methoxyphenylamino)methylene]malonate are recovered in the form of a brown viscous oil, with a quantitative yield.

Workup

  1. temperaturewithout cooling of the reaction mass
  2. additionAt the end of addition
  3. customhas reached 59° C
  4. waitkept at this temperature for 1 hour
  5. customis then removed by distillation at atmospheric pressure
  6. temperatureAfter cooling to 45° C.
  7. custom8.4 kg of diethyl 2-[(4-methoxyphenylamino)methylene]malonate are recovered in the form of a brown viscous oil, with a quantitative yield

Sources & evidence

ORD record
ord-33bcd0c87cc8454daebc90a097614cc4
Source dataset
uspto-grants-2008_07
Patent number
US07396934B2

Reaction notes

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