Cesium carbonate → HCID 59717866, Verbindung

HRID 2224686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2224686
[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). Step 3 {2-[4-(4-Acetyl-phenoxy)-phenyl]-ethyl}-carbamic acid ethyl ester

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-5fcb0093fd274bf8b5afd58dd010a998
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378448B2

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