Potassium Carbonate → 1,3,5-Tris(4-aminophenyl)benzene

Participants

Reaction Steps

1,3,5-tris(4-aminophenyl)benzene was prepared as described above in the preparation of compound 1. A mixture of 3 g of 1,3,5-tris(4-aminophenyl)-benzene, 22.2 g of m-iodotoluene, 5.9 g of potassium carbonate, 0.2 g of 18-crown-6 crown ether, 2.2 g of copper bronze and 40 ml of orthodichlorobenzene was flushed with argon and then the whole apparatus placed under vacuum. The mixture was then refluxed under argon for 120 hours. The reaction mixture was then filtered hot and the filtrate evaporated to dryness. High boiling point petroleum ether was then added and the product crystallized slowly in a deep freeze. It was then filtered off, dissolved in dichloromethane, precipitated with methanol and the precipitate, after drying, purified by preparative chromatographically using a 7:1 mixture of dichloromethane and n-hexane as the eluent. The 1,3,5-tris-(4-di-m -tolylaminophenyl)benzene produced had a melting point of 269.6° C.

Provenance & Evidence