Diethyl (ethoxymethylene)malonate → Diethyl 2-((4-iodophenylamino)methylene)malonate

HRID 1297604Notes

Reaction equation

HRID 1297604 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=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>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[CH:12][NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 108934-Iodoaniline

Product 1

HCID 4026452Diethyl 2-((4-iodophenylamino)methylene)malonateYield 90,490%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-iodoaniline (50 g, 0.23 mol) and diethyl ethoxymethylenemalonate (50.3 g, 0.23 mmol) was stirred at 90° C. for 10 hours. 150 mL of ethanol was added and the mixture was refluxed for 3 h. After cooling, the solid was collected, washed with hexane and dried over the oven to obtain 2-[(4-iodo-phenylamino)-methylene]-malonic acid diethyl ester (81 g, 91%) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperatureAfter cooling
  3. customthe solid was collected
  4. washwashed with hexane
  5. customdried over the oven

Sources & evidence

ORD record
ord-4a37bae800384567ac9f58bfdf31d523
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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