Aniline → HCID 86679339, compound

Participants

Reaction Conditions

Reaction Steps

A solution of TiCl4 (0.25 ml, 2.3 mmol) dissolved in chlorobenzene (5 ml) was slowly added at 80° C. to a mixture of the crude pentacenetetrone (4) (0.126 g), aniline (0.100 g, 0.11 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO) (1.3 g, 11.1 mmol) dissolved in chlorobenzene (25 ml). The reaction mixture was stirred for 3.5 hours at 130° C. The precipitate was then filtered with Celite and the resulting filtrate was concentrated. The residue was again dissolved in CHCl3 and was re-precipitated in a large amount of acetonitrile. The product was purified by silica gel column chromatography (CHCl3:hexane=3:1) to obtain N,N′,N″,N′″-tetraphenyl-2,3,9,10-tetramethyl-1,4,8,11-pentacenetetrone tetraimine (5) (0.0716 g, 0.103 mmol) at a yield of 25% with respect to 1,4:8,11-dicarboxy-5,14:7,12-diepoxy-4a,5,7,7a,11a,12,14,14a-octahydro-1,2,3,4,8,9,10,11-octaphenylpentacene (3).

Provenance & Evidence