4-Nitrobenzyl chloride → 4-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]aniline

Participants

Reaction Steps

A solution of 2-isopropylbenzimidazole (4.0 g, 25 mmol) in THF was treated with sodium hydride (1.00 g, 25 mmol, 60% dispersed in oil) under N2 atmosphere and stirred for 2 hr. 4-Chloromethyl-1-nitrobenzene (4.3 g, 25 mmol) was added and the reaction stirred for 16 hr. The reaction was worked by extraction from NaHCO3 with EtOAc×3, the combined organic layers were dried with MgSO4, filtered, and concentrated. This material was converted to the aniline as shown in Example 200. MS found: (M+H)=267.

Provenance & Evidence