Reaktion #1810325

Reaktionsgleichung

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

ethyl cyclopropanecarboximidate hydrochloride

ethanol

ammonia

→

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

Ausbeute 61.6%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe residue was purified twice by column chromatography over silica gel using first
5. 5
   workup.ADDITIONa mixture of trichloromethane and methanol (90:10 by volume)
6. 6
   workup.ADDITIONa mixture of trichloromethane and methanol (92:8 by volume) as eluent
7. 7
   SonstigeThe pure fractions were collected
8. 8
   Sonstigethe eluent was evaporated
9. 9
   SonstigeThe residue was crystallized from ethyl acetate

Vorschrift

A mixture of 3.3 parts of 4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 2.88 parts of ethyl cyclopropanecarboximidate hydrochloride and 64 parts of ethanol was stirred first for 4 hours at room temperature and further for 1 hour at reflux. The reaction mixture was cooled, treated with methanol, saturated with ammonia, and evaporated. The residue was purified twice by column chromatography over silica gel using first a mixture of trichloromethane and methanol (90:10 by volume) and then a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from ethyl acetate, yielding 2.57 parts (61.6%) of 2-cyclopropyl-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole; mp. 184.3° C. (compound 168).

Quelle