Thionyl Chloride → Acridine-9-carbonyl chloride hydrochloride
Reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O>>[ClH:20].[Cl:20][C:15]([C:13]1[C:14]2[C:5]([N:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2)=[O:17]Participants
Procedure
To 20 ml of thionyl chloride was suspended 0.84 g/3.74 mmol of acridine-9-carboxylic acid, and the suspension was refluxed under heat for 2 hours. Excessive thionyl chloride was distilled off the reaction mixture under reduced pressure to obtain 9-chlorocarbonyl acridine hydrochloride (1.0 g/96%). The resulting 9-chlorocarbonyl acridine hydrochloride and 0.3 g/1.61 mmol of 2,2'-biphenol were suspended in 50 ml of methylene chloride, and to this suspension were added 2 ml of triethylamine and a catalytic amount (44 mg/0.36 mmol) of dimethylaminopyridine in a stream of argon with stirring. The reaction mixture was stirred at room temperature for 2 hours, and then washed with 1N hydrochloric acid, distilled water, saturated aqueous solution of sodium hydrogencarbonate, and saturated aqueous solution of sodium chloride, in this order. The organic layer was dried with anhydrous sodium sulfate, and after removing the drying agent, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using hexane-methylene chloride for the eluting solution to obtain 0.85 g of the desired 2,2'-bis(acridine-9"-carbonyloxy)biphenyl. 1H-NMR (CDCl3): δ7.34-7.75 (20H, m), 8.18 (4H, d, JH =9 Hz).
Workup
- temperaturethe suspension was refluxed
- temperatureunder heat for 2 hours
- distillationExcessive thionyl chloride was distilled off the reaction mixture under reduced pressure
Sources & evidence
- ORD record
- ord-441295c3150b40f8aca250384d157b01
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087502
Reaction notes
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