Oxalyl chloride → Bis-(2,2,3,3-tetramethylcyclopropane) carbonyl benzimidazole

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Reaction Conditions

Reaction Steps

Bis-(2,2,3,3-tetramethylcyclopropane) carbonyl benzimidazole was synthesized as follows: oxalyl chloride (1.07 ml, 2 M in CH2Cl2) was added to 2,2,3,3-tetramethylcyclopropane carboxylic acid (0.305 g, 2.14 mmole) followed by one drop DMF. The mixture was allowed to react at RT for 1 hour. To the above solution was added 2-(4-aminophenyl)-6-amino benzimidazole (0.200 g, 0.89 mmole) in pyridine (2 ml). The reaction was heated to 60° C. overnight. The reaction was cooled and the precipitate filtered and washed with NaHCO3 and hexanes. The resulting solid was purified by preparative HPLC to yield a solid that was >99% pure.

Provenance & Evidence