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Ammonium Chloride → tert-butyl N'-[2-(2-chloroethoxy)-2-(4-fluorophenyl)acetyl]-hydrazinecarboxylate

HRID 546767
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546767
O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[Cl:16][CH2:17][CH2:18][O:19][CH:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:21]([OH:23])=O.[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[NH:32][NH2:33].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:16][CH2:17][CH2:18][O:19][CH:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:21]([NH:33][NH:32][C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:23]
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Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 70091tert-Butyl carbazateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66839523(2-Chloroethoxy)-(4-fluorophenyl)acetic acid

Produkt 1

HCID 66839491tert-butyl N'-[2-(2-chloroethoxy)-2-(4-fluorophenyl)acetyl]-hydrazinecarboxylateAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (4.38 g) was added to a solution of (2-chloroethoxy)-(4-fluorophenyl)acetic acid (2 g), tert-butyl carbazate (2.27 g) and triethylamine (3.58 mL) in tetrahydrofuran (20 mL), and the reaction solution was stirred at room temperature for 16 hours. Saturated aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex, elution solvent: heptane/ethyl acetate) to obtain the title compound (2.8 g). The property values of the compound are as follows.

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex, elution solvent: heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3bd53134f151472dbdb305eed5e484e3
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935815B2

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