1,10-Phenanthroline → HCID 16150869, compound

Participants

Reaction Steps

A 250 milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with N-phenyl-N-m-tolyl benzidine (8.0 grams, 0.023 mol), 4'-iodo-N-phenyl-N-m-tolyl-4-aminobiphenyl (17.5 grams, 0.038 mol), xylene (15 milliliters), 1,10-phenanthroline (0.34 gram, 1.9 mmol), cuprous chloride (0.188 gram, 1.9 mmol), and potassium hydroxide flakes (17.06 grams, 0.3 mol). Under an argon atmosphere, the reaction mixture was heated to reflux with an oil bath and allowed to proceed at that temperature until chromatographic analysis indicated that the reaction was complete after approximately 6 hours. The oil bath was removed and 100 milliliters of toluene and 25 milliliters of water were then added with efficient stirring. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase was washed with water and treated under argon with 25 grams of alumina. After the alumina was filtered off, the organic phase was evaporated to remove most of the toluene. The above product, Compound (1), was obtained by recrystallization of the residue from cyclohexane. Yield: 12.3 grams; m.p. 234.28° C.; Tg 134° C.

Provenance & Evidence