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Triethylamine → Phenyl[3-(4-fluoro-2-nitrophenoxy)propyl]carbamate

HRID 1477121
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1477121
C(N(CC)CC)C.[C:8](Cl)(=[O:16])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])=[C:21]([N+:30]([O-:32])=[O:31])[CH:20]=1>O1CCOCC1>[C:10]1([O:9][C:8](=[O:16])[NH:27][CH2:26][CH2:25][CH2:24][O:23][C:22]2[CH:28]=[CH:29][C:19]([F:18])=[CH:20][C:21]=2[N+:30]([O-:32])=[O:31])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 623484053-(4-Fluoro-2-nitrophenoxy)propylamine

Produkt 1

HCID 86641934Phenyl[3-(4-fluoro-2-nitrophenoxy)propyl]carbamateAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Triethylamine (2.90 ml, 21.4 mmol) and phenyl chlorocarbonate (2.52 ml, 20.0 mmol) were added to a dioxane solution (43 ml) of 3-(4-fluoro-2-nitrophenoxy)propylamine (4.03 g, 18.8 mmol), while being cooled with ice, and the mixture was stirred at room temperature for 0.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (dichloromethane:ethyl acetate=30:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 5.92 g of powdery yellow phenyl[3-(4-fluoro-2-nitrophenoxy)propyl]carbamate (yield: 94%).

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was then purified by silica gel column chromatography (dichloromethane:ethyl acetate=30:1)
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-128e26eee526476b83d0dec4424bced4
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09403773B2

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