Triethylamine → N-(2,6-Dimethoxyphenyl)-N'-[3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-yl]urea

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Reaction Steps

A solution of 3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-carboxylic acid (3 g), triethylamine (2.2 ml) and DPPA (2.9 ml) in benzene (200 ml) was stirred at room temperature for 1 hour, and then heated under reflux for 1 hour. After cooling to room temperature, to the reaction solution 2,6-dimethoxyaniline (1.6 g) was added and then heated under reflux for 1 hour. The reaction solution was combined with water and chloroform, and the organic layer was washed with diluted hydrochloric acid followed by a saturated aqueous solution of sodium hydrogen carbonate and water, and after drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resultant residue was purified by a silica gel column chromatography (eluent: chloroform), and further purified by recrystallization from THF-chloroform to obtain the title compound as a colorless crystal (2.4 g, 53%).

Provenance & Evidence