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

HRID 230835Notes

Reaction equation

HRID 230835 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>>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 108934-Iodoaniline

Product 1

HCID 4026452Diethyl 2-((4-iodophenylamino)methylene)malonate

Conditions

Temperature
60 °C

Procedure

A mixture of 4-iodoaniline (208 g) (available from Aldrich) and diethyl (ethoxymethylene)malonate (210 ml) (available from Aldrich) was heated to ca. 60° C., whereupon the mixture set solid. Heating was continued to 100° C., and then the mixture was removed from heating and broken up. Heating was continued at 100° C. for 1 h, and the solid was collected, washed with cyclohexane (1 L) and ethanol (2×500 ml), and dried in vacuo at 40° C. overnight to give the title compound as a white solid (356 g).

Workup

  1. temperatureHeating
  2. customwas continued to 100° C.
  3. customthe mixture was removed
  4. temperaturefrom heating
  5. temperatureHeating
  6. customthe solid was collected
  7. washwashed with cyclohexane (1 L) and ethanol (2×500 ml)
  8. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-849cd8a0c05c46a88550a47acd2ba304
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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