o-Nitrobenzonitrile → 2-([2-(Benzyloxy)ethyl]sulfanyl}benzonitrile

HRID 2070825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070825
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[CH2:12]([O:19][CH2:20][CH2:21][SH:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>CN(C=O)C.O>[CH2:12]([O:19][CH2:20][CH2:21][S:22][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 11922o-NitrobenzonitrileHCID 14797Potassium HydroxideHCID 14571805Ethanethiol, 2-(phenylmethoxy)-

Produkt 1

HCID 666890492-([2-(Benzyloxy)ethyl]sulfanyl}benzonitrileAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-nitrobenzonitrile (5.85 g) in DMF (20 mL) was treated with 2-(benzyloxy)ethanethiol (Example 320a, 6.64 g) and a solution of potassium hydroxide (3.76 g) in water (5 mL) was added dropwise under nitrogen. The resulting mixture was stirred at 0° C. for 2 h. The reaction was quenched with water and extracted into ethyl acetate. The combined organics were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified (SiO2 chromatography eluting with 50% diethyl ether in iso-hexane) to afford the subtitle compound as a solid (7.08 g). 1H NMR δ (CDCl3) 7.60 (d, 1H), 7.46 (d, 2H), 7.32-7.23 (m, 6H), 4.54-4.53 (m, 2H), 3.72 (t, 2H), 3.24 (t, 2H)

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted into ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. wash(SiO2 chromatography eluting with 50% diethyl ether in iso-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cf5890333d624af8a4e5fbc284b4bd9c
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299246B2

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