Diethyl (ethoxymethylene)malonate → HCID 13394075, compound

HRID 1583544Notes

Reaction equation

HRID 1583544 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C(O)C>[NH2:7][C:3]1[CH:2]=[C:1]([CH:6]=[CH:5][CH:4]=1)[NH:8][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7935M-Phenylenediamine

Product 1

HCID 13394075HCID 13394075, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.8 Grams of m-phenylenediamine are dissolved in 80 ml of ethyl alcohol, 21.6 grams of diethyl ethoxymethylenemalonate are added and the mixture is heated under reflux for 40 minutes. After filtration hot, 50 ml of water are added and the mixture is left for 24 to 36 hours at room temperature with stirring. The precipitate formed is filtered off, washed with an ethanol/water (1:1) mixture and dried at 60° C. The product is recrystallized in a benzene/hexane (2:1) mixture and 10.5 grams of a solid are obtained, of melting point 71°-74° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 40 minutes
  3. filtrationAfter filtration hot
  4. addition50 ml of water are added
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with an ethanol/water (1:1) mixture
  8. customdried at 60° C
  9. customThe product is recrystallized in a benzene/hexane (2:1) mixture and 10.5 grams of a solid
  10. customare obtained, of melting point 71°-74° C.

Sources & evidence

ORD record
ord-f5c33c5ba006448394ccdd9c63837021
Source dataset
uspto-grants-1985_11
Patent number
US04552882

Reaction notes

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