2,5-Dimethylaniline → n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

HRID 1371022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371022
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH2:9][C:10]2[CH:18]=[CH:17][C:13](C(O)=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CN(C1C2C([N:33]([CH3:35])C)=CC=CC=2C=CC=1)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.[CH3:53][C:54]1[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][C:55]=1[NH2:56]>C(#N)C>[CH3:53][C:54]1[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][C:55]=1[N:56]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])=[CH:18][CH:17]=1)[C:35]([NH2:33])=[O:43]

Komponenten

6

Edukt 4

HCID 72592,5-DimethylanilineHCID 88675Proton spongeHCID 199401P,P-Diphenylphosphinic azideHCID 185102554-[2-(4-Fluorophenyl)-2-oxoethyl]benzoic acid

Produkt 1

HCID 18510233n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoic acid (0.100 g, 0.387 mmol) in acetonitrile was added proton sponge ((0.083 g) and diphenylphosphoryl azide (0.106 g). The reaction mixture was refluxed for 30 minutes. 2,5-dimethyl aniline (0.047 g, 0.388 mmol) was added and the mixture was refluxed another 30 minutes. The reaction was quenched with HCl 1 M and extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified using flash chromatography eluting with hexane/ethyl acetate 40% to give (0.052 g) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturethe mixture was refluxed another 30 minutes
  3. customThe reaction was quenched with HCl 1 M
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified
  9. washeluting with hexane/ethyl acetate 40%

Quellen und Nachweise

ORD-Eintrag
ord-72d4cbd6606a4cda93c73c9c3908ad8e
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583126B2

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