Diphenyl Ether → HCID 178469546, compound

HRID 131539Notes

Reaction equation

HRID 131539 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH:23]=[C:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([O:27]CC)=O)=[CH:18][CH:17]=1)#[N:15]>CCCCCC>[CH2:33]([O:32][C:30]([C:24]1[CH:23]=[N:22][C:19]2[C:18]([C:25]=1[OH:27])=[CH:17][C:16]([C:14]#[N:15])=[CH:21][CH:20]=2)=[O:31])[CH3:34]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 1989756Diethyl [(4-cyanoanilino)methylidene]propanedioate

Product 1

HCID 178469546HCID 178469546, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 100 mL vigorously refluxing diphenyl ether (Aldrich) was added in open air, in portions over the course of one hour, 10.5 g (36.5 mmol) diethyl 2-(4-cyanophenylamino)methylenemalonate. The solution was refluxed for one additional hour. After allowing the solution to cool to below 100° C., it was poured into 200 mL hexane. The resulting precipitate was filtered and washed well with hexane to yield 8.39 g (34.6 mmol, 94%) of the title compound as a light brown solid: MH+: 243, mp>265° C.

Workup

  1. temperatureThe solution was refluxed for one additional hour
  2. temperatureto cool to below 100° C.
  3. filtrationThe resulting precipitate was filtered
  4. washwashed well with hexane

Sources & evidence

ORD record
ord-559b89eeac59485d80dda823f882debe
Source dataset
uspto-grants-2008_06
Patent number
US07384958B2

Reaction notes

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