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Triethylamine → N-(4-Fluorophenyl)-N'-(2-fluoro-4-hydroxyphenyl)cyclopropane-1,1-dicarboxamide

HRID 2066250
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2066250
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([OH:16])=O)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:52][C:53]1[CH:58]=[CH:57][C:56]([OH:59])=[CH:55][C:54]=1[F:60]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2([C:14]([NH:52][C:53]3[CH:58]=[CH:57][C:56]([OH:59])=[CH:55][C:54]=3[F:60])=[O:16])[CH2:12][CH2:13]2)=[O:10])=[CH:6][CH:7]=1
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidHCID 448869124-Amino-3-fluorophenol hydrochloride

Produkt 1

HCID 59596967N-(4-Fluorophenyl)-N'-(2-fluoro-4-hydroxyphenyl)cyclopropane-1,1-dicarboxamide
Ausbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-fluorophenylcarbamoyl)cyclopropanecarboxylic acid (1.02 g) in N,N-dimethylformamide (5.0 ml) were added triethylamine (1.28 ml) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.03 g), followed by stirring at room temperature for 5 min. To this was added 4-amino-3-fluorophenol hydrochloride (500 mg), followed by stirring at room temperature for 3 days. The reaction mixture was partitioned between ethyl acetate and a 1N aqueous solution of sodium hydroxide. The organic layer was washed with a 1N aqueous solution of sodium hydroxide. To the aqueous layer was added 5N hydrochloric acid to make it acidic, this was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:3 to 1:2). Fractions containing the target compound were concentrated under reduced pressure to provide the titled compound as a pale red solid (395 mg, 39%).

Aufarbeitung

  1. stirringby stirring at room temperature for 3 days
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide
  4. additionTo the aqueous layer was added 5N hydrochloric acid
  5. extractionthis was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed
  9. customthe residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:3 to 1:2)
  10. additionFractions containing the target compound
  11. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f2d05b8f36634f6d93d7b70d97690af8
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08288538B2

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