Reaction #1509649

Reaction equation

hexacenetetrone

2,3,10,11-tetramethyl-1,4,9,12-hexacenetetrone

aniline

1,4-diazabicyclo[2.2.2]octane

→

N,N′,N″,N′″-tetraphenyl-2,3,10,11-tetramethyl-1,4,9,12-hexacenetetrone tetraimine

Yield 56.5%

Solvents

chlorobenzene

chlorobenzene

Conditions

Workup

1. 1
   ConcentrationThis reaction mixture was then concentrated
2. 2
   workup.DISSOLUTIONThe residue was again dissolved in CHCl3
3. 3
   Otherre-precipitated in a large amount of acetonitrile
4. 4
   FiltrationThe precipitate was then filtered with Celite
5. 5
   Washwashed with acetonitrile and MeOH
6. 6
   Otherdried in a vacuum

Procedure

A solution of TiCl4 (0.15 ml, 1.4 mmol) dissolved in chlorobenzene (5 ml) was slowly added at 75° C. to a mixture of the crude hexacenetetrone (10) (0.118 g), aniline (0.15 ml, 1.6 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.900 g, 8.0 mmol) dissolved in chlorobenzene (20 ml). The reaction mixture was then stirred for 1.5 hours at 125° C. This reaction mixture was then concentrated by passing through a silica gel column (CHCl3). The residue was again dissolved in CHCl3 and re-precipitated in a large amount of acetonitrile. The precipitate was then filtered with Celite, washed with acetonitrile and MeOH, and dried in a vacuum to obtain N,N′,N″,N′″-tetraphenyl-2,3,10,11-tetramethyl-1,4,9,12-hexacenetetrone tetraimine (11) (0.0560 g, 0.075 mmol) at a yield of 25% with respect to 1,4:9,12-dicarboxy-5, 16:8,13-diepoxy-4a,5,8,8a,12a,13,16,16a-octahydro-1,2,3,4,9,10,11,12-octaphenylhexacene (9).

Source