2,6-Dimethylaniline → HCID 18688887, compound

Participants

Reaction Steps

To a stirred mixture of 400 mg of 3-(2-chlorophenyl)-6,7-dihydro-5H-cyclopenta[f][1]benzothiophene-2-carboxylic acid and 0.27 cc of diphenylphosphoryl azide in 5 cc of benzene was added dropwise 0.175 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 15 minutes and then heated under reflux for 30 minutes. After cooling, 0.155 cc of 2,6-dimethylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and the desired compound was extracted with chloroform. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=15/85) to obtain 454 mg of compound 87.

Provenance & Evidence