1,4-Dichlorobenzene → Methyl 4-(5,6-dinitro-1H-benzimidazol-2-yl)benzoate

Participants

Reaction Steps

To a solution containing 10 g (45.8 mmole) of p-chlorocarbonylmethylbenzoate dissolved in 100 ml of dichlorobenzene was added 3.0 g (15.3 mmole) of 1,2-diamino-4,5-dinitrobenzene. After heating the resulting mixture to reflux under nitrogen (frothing), it was maintained at that temperature for 2 hours. The solution was then allowed to cool in ice for one hour, and the precipitate that formed was filtered by suction, washed with benzene and air-dried. Recrystallization from tetrahydrofuran (THF)-n-propanol by distillation to a small volume in vacuo yielded 3.2 g (62%) of 2-[p-carbomethoxyphenyl]-5,6-dinitrobenzimidazole as light yellow needles, m.p. 239°-240°.

Provenance & Evidence