Diethyl (ethoxymethylene)malonate → HCID 59416172, compound

HRID 2061847Notes

Reaction equation

HRID 2061847 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].CCO[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 59416172HCID 59416172, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-fluoro-4-iodoaniline (15 g, 63.29 mmol) and diethyl ethoxymethylene malonate (41.05 g, 0.19 mol) in toluene (75 mL) was heated to reflux with a Dean-Stark condenser for 7 h. The mixture was cooled, concentrated and washed with methyl tert-butyl ether (500 ml). The methyl tert-butyl ether layer was then concentrated and the residue was washed with heptane (500 ml), yielding a white solid that precipitated out of the yellow solution. This solid was then collected, yielding 23.6 g (91%) of diethyl 2-((2-fluoro-4-iodophenylamino)methylene)malonate.

Workup

  1. temperatureto reflux with a Dean-Stark condenser for 7 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. washwashed with methyl tert-butyl ether (500 ml)
  5. concentrationThe methyl tert-butyl ether layer was then concentrated
  6. washthe residue was washed with heptane (500 ml)
  7. customyielding a white solid
  8. customthat precipitated out of the yellow solution
  9. customThis solid was then collected

Sources & evidence

ORD record
ord-1a0176691642466199ea9185afa3fd56
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

Loading…