Reaktion #1810319

Reaktionsgleichung

ammonium hydroxide

4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine

ethyl 2-chlorobenzoate

→

2-(2-chlorophenyl)-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole

Ausbeute 26.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigecrushed ice
2. 2
   ExtraktionThe product was extracted three times with 120 parts of trichloromethane
3. 3
   SonstigeThe combined extracts were dried
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column chromatography (HPLC) over silica gel using
7. 7
   workup.ADDITIONa mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.05 by volume) as eluent
8. 8
   SonstigeThe pure fractions were collected
9. 9
   Sonstigethe eluent was evaporated
10. 10
    SonstigeThe residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane
11. 11
    FiltrationThe product was filtered off
12. 12
    Sonstigedried in vacuo at 100° C.

Vorschrift

A mixture of 5 parts of 4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 5 parts of ethyl 2-chlorobenzoate and 30 parts of polyphosphoric acid was stirred for 4 hours at 140° C. The whole was poured into 200 parts of water and crushed ice. The mixture was treated with ammonium hydroxide. The product was extracted three times with 120 parts of trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography (HPLC) over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.05 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane. The product was filtered off and dried in vacuo at 100° C., yielding 2.1 parts (26%) of 2-(2-chlorophenyl)-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole; mp. 115.2° C. (compound 88).

Quelle