Diethyl (ethoxymethylene)malonate → HCID 68577453, compound

HRID 638990Notes

Reaction equation

HRID 638990 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].NC1C=CC=CC=1.C([O:20][CH:21]=[C:22]([C:28](OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]2[C:3]=1[NH:4][CH:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:21]2=[O:20]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 86616781HCID 86616781, compound

Product 1

HCID 68577453HCID 68577453, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

A mixture of aniline 2-fluoro-4-(methoxy)aniline (22.8 g, 162 mmol) and diethyl [(ethyloxy)methylidene]propanedioate (32.6 mL) were heated to reflux in Dowtherm A under a flow of argon. After 15 minutes (when all ethanol was removed), the mixture was allowed to cool down and was diluted with pentane. A precipitate was formed which was triturated with pentane, filtered and dried under vacuum to afford the product as an oil (33.06 g, 77%); MS (+ve ion electrospray) m/z 265 (M+H)+.

Workup

  1. temperaturewere heated
  2. customAfter 15 minutes (when all ethanol was removed), the mixture
  3. temperatureto cool down
  4. additionwas diluted with pentane
  5. customA precipitate was formed which
  6. customwas triturated with pentane
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-554cc37a3899427083a520e32e0ce368
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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