Dimethylformamide → HCID 86679916, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Intermediate A (1.05 g, 3.0 mmol), diphenylamine (2.03 g, 12.0 mmol), potassium carbonate (1.66 g, 12.0 mmol), CuI (1.14 g, 6.0 mmol), and dimethylformamide (20 mL) was stirred under argon and heated at 160° C. for 3 days. After cooling, the reaction mixture was poured into water (100 mL) and stirred for 15 minutes. The precipitate was filtered off and washed with water (50 mL). A suspension of this solid in dichloromethane (100 mL) was treated with concentrated ammonium hydroxide (20 mL) and stirred for 1 hour. The dichloromethane layer was separated, dried over sodium sulfate and chromatographed (silica gel, dichloromethane/ethyl acetate 9:1). The obtained product was recrystallized from ethanol to give 4,7-bis(N,N-diphenylamino)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole (Example 19), orange crystals, 55 mg (3%). 1H NMR (400 MHz, CDCl3): δ 8.57 (m, 2H, pyridine), 7.64 (m, 2H, pyridine), 7.28 (m, 8H, Ph), 7.15 (m, 8H, Ph), 7.06 (t, J=7.3 Hz, 4H, Ph), 6.96 (s, 2H, benzotriazole. UV-vis spectrum (dichloromethane): λmax=471 nm. Fluorimetry (dichloromethane): λmax=640 nm.

Provenance & Evidence