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

HRID 2061845Notes

Reaction equation

HRID 2061845 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:11]OCC)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[I:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[I:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH:11]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 108934-Iodoaniline

Product 1

HCID 4026452Diethyl 2-((4-iodophenylamino)methylene)malonateYield 77.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethoxymethylene malonic acid diethyl ester (20.1 mL, 0.10 mol) and 4-iodoaniline (22 g, 0.10 mole) in toluene (300 ml) was heated to reflux for 1 h. After this period of time, solvents were removed under vacuum, and the crude material was precipitated in methyl tert-butyl ether and the resulting white solid was filtered, and dried under vacuum to give 30 g product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customAfter this period of time, solvents were removed under vacuum
  4. customthe crude material was precipitated in methyl tert-butyl ether
  5. filtrationthe resulting white solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7b1b99b73fa643798bfc611bb71139f8
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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