Diethyl (ethoxymethylene)malonate → HCID 178469636, compound

HRID 611993Notes

Reaction equation

HRID 611993 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC>[C:17]([C:16]1[CH:22]=[N:1][C:2]2[C:7]([C:15]=1[OH:14])=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=2)([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 227703,4-Dimethoxyaniline

Product 1

HCID 178469636HCID 178469636, compound

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 30.6 g of 4-aminoveratrole and 43.2 g of diethyl ethoxymethylenemalonate was heated at 100 for 2 h and at 165° C. for 0.75 h. The intermediate thus obtained was dissolved in 600 ml of diphenyl ether, and the resulting solution was heated at reflux temperature for 2 h, cooled, and diluted with hexane. The resulting solid was filtered, washed with hexane followed by ether, and dried to provide the tide compound as a brown solid, mp 275-285° C.

Workup

  1. customThe intermediate thus obtained
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux temperature for 2 h
  4. temperaturecooled
  5. filtrationThe resulting solid was filtered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-e2e52782ddd34621927539afb5255454
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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