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

HRID 1874868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874868
[C:1]([CH:3]([NH:13][C:14](=O)[CH2:15][CH3:16])[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:38]>C(#N)C>[Cl:38][C:1]1[N:2]=[C:14]([CH2:15][CH3:16])[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 59451375N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}propanamide

Produkt 1

HCID 594516374-chloro-2-ethyl-5-{[(phenylmethyl)oxy]methyl}-1H-imidazoleAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}propanamide (3.62 g, 15.6 mmol), triphenylphosphine (10.2 g, 39.0 mmol), and carbon tetrachloride (3.8 mL, 39.0 mmol) in acetonitrile (150 mL) was heated at 45° C. for 4.5 h. The reaction was concentrated and the residue was stirred in CH2Cl2 (170 mL) and 0.5 N NaOH (150 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-50% EtOAc:hexanes) to give the title compound (2.51 g, 64%) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.29-7.38 (m, 5H), 4.52 (s, 2H), 4.50 (s, 2H), 2.65 (q, 2H), 1.26 (t, 3H). ES-LCMS: m/z 250.6, 252.9 (M+H).

Aufarbeitung

  1. concentrationThe reaction was 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 (5-50% EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-12cf6e9dc7f347a6ba91c7196a7d8d8f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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