Cesium carbonate → HCID 59717866, Verbindung

HRID 601573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601573
[CH2:1]([O:3][C:4](=[O:15])[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:2].F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:15])[NH:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:12][CH:13]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 145174-FluorobenzonitrileHCID 2762412Ethyl N-[2-(4-hydroxyphenyl)ethyl]carbamate

Produkt 1

HCID 59717866HCID 59717866, VerbindungAusbeute 119,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Combine 6.2 mmol of [2-(4-hydroxy-phenyl)-ethyl]-carbamic acid ethyl ester (3.6.0 g, 17.2 mmol), 4-fluorobenzonitrile (2.1 g, 17.2 mmol), cesium carbonate (11.2 g, 34.4 mmol), and N,N-dimethylformamide (80 mL), stir and heat at 85° C. for 18 hours. Cool to room temperature and evaporate on a rotary evaporator, took up residue in brine then extracted with ethyl acetate (3×50 mL). Dry the combined ethyl acetate extracts over sodium chloride/magnesium sulfate, filter, and concentrate on a rotary evaporator to yield the crude product (4.5 g). The crude product is purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes to yield {2-[4-(4-cyano-phenoxy)-phenyl]-ethyl}-carbamic acid ethyl ester (2.3 g): 1H NMR (CDCl3, 300.00 MHz): 7.66-7.60 (m, 2H), 7.31-7.24 (m, 2H), 7.07-7.00 (m, 4H), 4.72 (s, 1H), 4.16 (q, 2H, J=7.0 Hz), 3.48 (q, 2H, J=6.7 Hz), 2.86 (t, 2H, J=7.0 Hz), 1.27 (t, 3H, J=7.0 Hz).

Aufarbeitung

  1. temperatureCool to room temperature
  2. customevaporate on a rotary evaporator
  3. extractionthen extracted with ethyl acetate (3×50 mL)
  4. dry with materialDry the combined ethyl acetate
  5. filtrationfilter
  6. concentrationconcentrate on a rotary evaporator
  7. customto yield the crude product (4.5 g)
  8. customThe crude product is purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-880e5fbf8f17441a8cb08df87cfc0a3d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902372B2

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