Reaction #2358557

Reaction equation

Anthraquinone-2,7-disulfonylchloride

diisopropylethylamine

→

yellow compound 1-27

Yield 91.0%

2,7-bis(azocan-1-ylsulfonyl)anthracene-9,10-dione

Yield 91.0%

Solvents

DCM

Conditions

Workup

1. 1
   OtherSolvent was evaporated
2. 2
   workup.ADDITIONthe residue was treated with 1N HCl
3. 3
   Filtrationfiltered off
4. 4
   Washwashed with water
5. 5
   Otherdried
6. 6
   OtherCrude material was crystallized from chloroform-hexane

Procedure

Anthraquinone-2,7-disulfonylchloride (1215 mg, 3 mmole) was dissolved in 100 mL DCM. The solution was cooled to −50° C. To this solution was added 1 mL (8 mmole) of heptamethyleneimine, followed by 1 mL of diisopropylethylamine. The reaction mixture was stirred at room temperature for 4 hrs. Solvent was evaporated and the residue was treated with 1N HCl, filtered off, washed with water and dried. Crude material was crystallized from chloroform-hexane to give 1.014 g (91%) of yellow compound 1-27. H1—NMR (CDCl3): 8.70 (2H, d, C1 and C8), 8.47 (2H, d, C4 and C5), 8.22 (2H, dd, C3 and C6), 3.22 (8H, m), 1.70 (20H, m).

Source