4-tert-Butylbenzoyl chloride → HCID 178440953, compound

Participants

Reaction Steps

By methods substantially equivalent to those described in Examples 1-B and 1-C, 3.7 g (6.5 mmol) of crude 2-[(4-t-butylbenzoyl)amino]-N-(1-tosylbenzimidazol-6-yl)benzamide was prepared from 2-nitro-N-(1-tosylbenzimidazol-6-yl)benzamide and 4-t-butylbenzoyl chloride. This material was dissolved in p-dioxane (50 mL) and a solution of LiOH.H2O (0.48 g, 11 mmol) in water (25 mL) was added with vigorous stirring. After 16 h, the solvents were removed in vacuo and the residue was partitioned between chloroform and satd aq NaHCO3. The phases were separated and the organic phase was washed with water, followed by brine, then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether, filtered and the solid was dissolved in a minimal amount of chloroform and chromatographed over a silica gel column with 10% methanol/chloroform. The product containing fractions were combined and concentrated in vacuo to give 0.97 g (36% overall) of off-white solid.

Provenance & Evidence