Triethylamine → HCID 58243728, Verbindung

HRID 389084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389084
C1C=CC2N(O)[N:8]=[N:7]C=2C=1.[F:11][C:12]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:13]=1[O:14][C:15]([CH3:20])([CH3:19])[C:16](O)=[O:17].O.NN.C(N(CC)CC)C>C(#N)C>[F:11][C:12]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:13]=1[O:14][C:15]([CH3:20])([CH3:19])[C:16]([NH:7][NH2:8])=[O:17]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 15318012-(2,4-Difluorophenoxy)-2-methylpropanoic acid

Produkt 1

HCID 58243728HCID 58243728, VerbindungAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

HOBt (1.76 g) and WSC•monohydrochloride (2.49 g) were added to a solution of 2-(2,4-difluorophenoxy)-2-methylpropanoic acid (2.34 g) in acetonitrile (27 ml), followed by stirring at room temperature for one hour. This solution was added dropwise to a solution of hydrazine monohydrate (3.25 g) and triethylamine (3.0 ml) in acetonitrile (20 ml) under ice cooling, followed by stirring at room temperature for 2 hours, the reaction solution was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=98:2) to obtain 2-(2,4-difluorophenoxy)-2-methylpropanohydrazide (1.74 g).

Aufarbeitung

  1. stirringby stirring at room temperature for 2 hours
  2. concentrationthe reaction solution was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate
  3. additionwas added
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=98:2)

Quellen und Nachweise

ORD-Eintrag
ord-d3ff1945a2d1415581c0edf84f74c947
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377923B2

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