Carbon Tetrachloride → 4-chloro-5-{[(phenylmethyl)oxy]methyl}-2-propyl-1H-imidazole

HRID 1874874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874874
[C:1]([CH:3]([NH:13][C:14](=O)[CH2:15][CH2:16][CH3:17])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>C(#N)C>[Cl:39][C:1]1[N:2]=[C:14]([CH2:15][CH2:16][CH3:17])[NH:13][C:3]=1[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 594513703-Benzyloxy-a-(N-butyryl)-aminopropionitrile

Produkt 1

HCID 594513894-chloro-5-{[(phenylmethyl)oxy]methyl}-2-propyl-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}butanamide (1.60 g, 6.5 mmol), triphenylphosphine (4.3 g, 16.3 mmol), and carbon tetrachloride (1.6 mL, 16.3 mmol) in acetonitrile (65 mL) was heated at 42° C. for 12 h. The reaction was then concentrated and the residue was stirred in CH2Cl2 (70 mL) and 0.5 N NaOH (60 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-40% EtOAc:hexanes) to give the title compound as a light yellow solid, in assumed quantitative yield due to inseparable triphenylphosphine oxide. 1H NMR (400 MHz, CDCl3) δ 7.30-7.40 (m, 5H), 4.52 (s, 4H), 2.58-2.68 (m, 2H), 1.68-1.82 (m, 2H), 0.97 (t, 3H).

Aufarbeitung

  1. concentrationThe reaction was then concentrated
  2. customThe organic layer was isolated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel flash column chromatography (5-40% EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1a4f210af72d457085213dad455d377e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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