Reaktion #1509606

ord-6e54eea001d84b1bb0f6ba30bd45186d

Reaktionsgleichung

c1ccc(Cn2ccnc2)cc1
1-Benzylimidazole
OCC(O)CCl
3-chloro-1,2-propanediol
OCC(O)C[n+]1ccn(Cc2ccccc2)c1.[Cl-]
product
Ausbeute 97.0%
OCC(O)C[n+]1ccn(Cc2ccccc2)c1.[Cl-]
1-(2,3-Dihydroxypropyl)-3-benzylimidazolium Chloride
Ausbeute 97.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigetransferred to a tared flask
  2. 2
    Einengenconcentrated

Vorschrift

1-Benzylimidazole (3.95 g, 25.0 mmol) and 3-chloro-1,2-propanediol (2.76 g, 25.0 mmol) were stirred in a 130° C. oil bath for 48 h, after which the flask was placed under vacuum and stirring continued at 130° C. for another 48 h. The residue was then dissolved in CH3OH and transferred to a tared flask and concentrated to afford the product as a viscous brown oil (6.50 g, 97%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 3.18-3.30 (m, 1H) 3.37-3.49 (m, 1H) 3.73-3.86 (m, 1H) 4.15 (dd, J=13.74, 7.69 Hz, 1H) 4.36 (dd, J=13.74, 3.11 Hz, 1H) 5.21 (t, J=5.50 Hz, 1H) 5.49 (s, 2H) 5.62 (d, J=5.50 Hz, 1H) 7.32-7.50 (m, 5H) 7.80 (t, J=1.83 Hz, 1H) 7.86 (t, J=1.83 Hz, 1H) 9.49 (t, J=1.56 Hz, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08926732B2uspto-grants-2015_01